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[ CAS No. 89-77-0 ] {[proInfo.proName]}

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Chemical Structure| 89-77-0

Chemical Structure| 89-77-0

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Quality Control of [ 89-77-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 89-77-0 ]

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Product Details of [ 89-77-0 ]

CAS No. :	89-77-0	MDL No. :	MFCD00007778
Formula :	C₇H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	NH₂C₆H₃(Cl)CO₂H	InChI Key :	JYYLQSCZISREGY-UHFFFAOYSA-N
M.W :	171.58	Pubchem ID :	66646
Synonyms :

Calculated chemistry of [ 89-77-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.82
TPSA :	63.32 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.22
Log Po/w (XLOGP3) :	1.57
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	1.01 mg/ml ; 0.00588 mol/l
Class :	Soluble
Log S (Ali) :	-2.51
Solubility :	0.53 mg/ml ; 0.00309 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	1.63 mg/ml ; 0.00948 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.06

Safety of [ 89-77-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89-77-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 89-77-0 ]
Downstream synthetic route of [ 89-77-0 ]

[ 89-77-0 ] Synthesis Path-Upstream 1~5

1
[ 57-13-6 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 200℃; for 1 h;	Step A: Preparation of 7-chloro-1H-quinazoline-2,4-dione. A mixture of 2-amino-4-chlorobenzoic acid (2.00 g, 11.6 mmol) and urea (2.80 g, 46.6 mmol) was heated to 200° C. for 1 h. The mixture was allowed to cool to room temperature and the resulting mass was triturated well with water. The product was collected by filtration (2.30 g, 100percent). The MS and NMR data are in agreement with those that have been previously described: Organic Process Research and Development, 2003, 7, 700-706. ¹H NMR (600 MHz, DMSO-d₆): 12.00 (br s, 2H), 8.59-8.53 (m, 1H), 7.93-7.80 (m, 2H).

Reference： [1] Patent: US2010/204226, 2010, A1, . Location in patent: Page/Page column 22
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7268 - 7274
[3] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[4] Patent: DE931845, 1952, ,
[5] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 7, p. 478 - 483[6] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 7, p. 802 - 807
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 7, p. 3075 - 3093
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156

2
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Journal of the Chemical Society, 1948, p. 1759,1765
[2] Patent: US5688803, 1997, A,
[3] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 8, p. 824 - 829

3
[ 590-28-3 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433

4
[ 917-61-3 ]
[ 89-77-0 ]
[ 13165-35-0 ]

Reference： [1] Patent: US6344559, 2002, B1, . Location in patent: Page column 4

5
[ 89-77-0 ]
[ 208465-21-8 ]

Reference： [1] Patent: CN106243046, 2016, A,

[ 89-77-0 ] Synthesis Path-Downstream 1~11

1
[ 5900-59-4 ]
[ 89-77-0 ]

Reference： [1]Journal of the American Chemical Society,1923,vol. 45,p. 1028

2
[ 108-94-1 ]
[ 89-77-0 ]
[ 334504-68-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 842,844
Chemisches Zentralblatt,1939,vol. 110,p. 1366
[2]Journal of Organic Chemistry,1947,vol. 12,p. 567,570

3
[ 89-77-0 ]
[ 37585-16-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	26.5 g (0.7 mol) of lithium tetrahydroaluminum and dry tetrahydrofuran (300 mL) were added dropwise to a mixture of 100 g of 2-amino-4-chlorobenzoic acid (0.58 mol) and dry tetrahydrofuran (800 mL) under nitrogen atmosphere. The solution was added dropwise, and stirred at room temperature for 2 hours, diluted with 10 mL of water, and a solution of 20 g of sodium hydroxide and 100 mL of water was added.Filtration, the filtrate was extracted with EtOAc. The concentrate was crystallized from ethyl acetate/petroleum ether.82.7 g of 2-amino-4-chloro-benzyl alcohol was obtained (yield: 90%).
88%	With borane-THF; In tetrahydrofuran; at 0 - 30℃; for 1.66667h;Inert atmosphere;	General procedure: To a solution of 6-chloroanthranilic acid (1.5 g, 8.74 mmol) in THF (5 mL) was added dropwise 1.08 M borane-tetrahydrofuran complex in THF (24.3 mL, 26.2 mmol) at 0 C under an Ar atmosphere for 10 min. After 1.5 h with stirring at 30 C, the solution was cooled at 0 C, added aqueous THF (THF/H2O = 1:1, 60 mL) and potassium carbonate, and extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was crystallized from AcOEt to give 1a (1.2 g, 88%) as a white needle crystal.
85.4%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere;	To a mixture of L1AIH4 (4.4 g, 116.6 mmol) in dry THF (116 mL) at 0C under N2 was added dropwise a solution of 2-amino-4-chlorobenzoic acid (10 g, 58.3 mmol) in dry THF (80 mL). The mixture was stirred at r.t. for 2 hr, then quenched, in sequence, by addition of H2O (4 mL), aq. NaOH (15 wt, 8 mL), and H2O (12 mL). The resulting mixture was filtered, and the filtrate was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The residue was re -crystallized from EtOAc/PE to give (2-amino-4-chlorophenyl)methanol (7.8 g, 85.4% yield). LC-MS: m/z 158(M+H)+.

81.6%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 8h;Inert atmosphere;	In a 500 niL round bottom flask, the stirred solution of 2-amino-4-chlorobenzoic acid (42.8 g, 250.29 mmol, Aldrich) was dissolved anhydrous THF (200 mL) and the solution was cooled in an ice-bath. Lithium aluminum hydride (11.76 g, 312.86 mmol) was added portionwise to the above solution at the ice-bath temperature under nitrogen atmosphere. The resulting mixture was stirred at rt for 8 h. On completion of reaction the reaction mixture was cooled to ice-bath temperature and quenched by sequential addition of cold water (12 mL), 15% NaOH (12 mL) and water (36 mL). The resulting slurry was stirred at rt for 30 min and filtered through a CELITE pad. The solid residue was washed with ethyl acetate (1000 mL) and combined filtrate was concentrated under reduced pressure to give (2-amino 4-chlorophenyl)methanol as an off white solid. Yield: 32g (81.6 %). LCMS (ESI, m/z): 181 (M+23)+.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 8h;	2-amino-4-chlorobenzoic acid(42. 8g, 0. 25mol) dissolved in 200 ml of THF anhyride to, cooled in an ice water bath. In this solution, lithium aluminum piece (11. 76g, 0. 31mol) is added. The mixture is stirred at room temperature for 8 hours. 12g of water is added, 12g of the next 15% NaOH is added. Next, 36g of the added water. The slurry is stirred at room temperature for 30 minutes. The slurry is filtered. Solid washed with ethyl acetate. Liquid are together, the solvent is evaporated. Its meleimide without purifying substance is used in the next step.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2h;Cooling with ice;	General procedure: To a stirred solution of anthranilic acid (15 mmol) in tetrahydrofuran (1 M, 15 mL) was slowly added Lithium aluminum hydride solution 1M in THF (30mL, 30 mmol, 2 eq.) in an ice bath. Upon completion of the addition, the ice bath was taken away, and stirring was continued for 2 hours at the room temperature. The reaction was quenched with water and a 5% solution of NaOH in water. The inorganic solid residue was filtered under vacuum, washed with ethyl acetate and the filtrate was transferred to a separatory funnel. The two layers were separated, and the product was extracted with ethyl acetate (x3). The organic phase was washed with brine (x1), dried over sodium sulfate, concentrated under reduced pressure and used in the next step without further purification.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere;	General procedure: A solution of the LiAlH4 (1.5 equiv) in anhydrous THF (50 mL) was stirred at 0 C, while 2-amino-benzoic acid (1.0 equiv) in THF was added dropwise. Then the mixture was warmed to room temperature and stirred for 2 hours. After complete consumption of the acid, the mixture was quenched with 10 % NaOH. The resulting suspension was filtered and extracted with ethyl acetate. The combined organic collection was evaporated. The residue was purified by column chromatography to give the product S1 as a white solid or off-white solid.

Reference： [1]ACS Catalysis,2013,vol. 3,p. 622 - 624
[2]Chemical Communications,2017,vol. 53,p. 216 - 219
[3]Organic Letters,2017,vol. 19,p. 3219 - 3222
[4]Patent: CN108997437,2018,A .Location in patent: Paragraph 0041; 0042; 0043
[5]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831
[6]Patent: WO2016/112088,2016,A1 .Location in patent: Paragraph 0214
[7]Patent: WO2013/188724,2013,A1 .Location in patent: Paragraph 00128
[8]Organic Letters,2019,vol. 21,p. 4703 - 4708
[9]Synlett,1997,vol. 1997,p. 704 - 706
[10]Chemistry - A European Journal,2012,vol. 18,p. 5530 - 5535
[11]Tetrahedron,2014,vol. 70,p. 5114 - 5121
[12]Angewandte Chemie - International Edition,2014,vol. 53,p. 9603 - 9607,5
Angew. Chem.,2014,vol. 126,p. 9757 - 9761,5
Angewandte Chemie,2014,vol. 126,p. 9757 - 9761,5
[13]Organic Letters,2015,vol. 17,p. 4750 - 4753
[14]Patent: JP2015/212297,2015,A .Location in patent: Paragraph 0150; 0151
[15]Organic and Biomolecular Chemistry,2016,vol. 14,p. 8966 - 8970
[16]Tetrahedron Letters,2017,vol. 58,p. 4264 - 4268
[17]Tetrahedron Letters,2019,vol. 60,p. 1967 - 1970
[18]Journal of the American Chemical Society,2020,vol. 142,p. 3636 - 3644

4
[ 89-77-0 ]
A - 2-hydroxymethyl 5-chloroaniline* [ No CAS ]
[ 37585-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; hydrogen; In tetrahydrofuran; water; Petroleum ether;	Step A - 2-hydroxymethyl 5-chloroaniline* may also be called 2-amino-4-chlorobenzyl alcohol STR20 To a 500 ml vessel equipped with a mechanical stirrer is added 220 ml of tetrahydrofuran (freshly distilled from lithium aluminum hydride). The mixture is cooled to 0, and 6 g of lithium aluminum hydride is then slowly added to the mixture. The temperature of the mixture is maintained at 0 to 20, while 17.159 g of 4-chloroanthranilic acid is slowly added in small portions to the mixture (vented to atmosphere). The mixture is then, slowly warmed to room temperature, then refluxed for 16 hrs. The mixture is then cooled to 0 in an ice bath and 6 ml. of water slowly added (causing evolation of hydrogen). From 6 to 8 ml of 20% aqueous sodium hydroxide are then added to the mixture dropwise. The mixture becomes thicker and more difficult to stir, and a solid form upon addition of 18 ml of water (at 0). 70 ml of tetrahydrofuran is added and the mixture stirred at room temperature for 2 hrs. The solids are recovered by filtration, digested in 100 ml of tetrahydrofuran and filtered again; the filtrates being retained and combined, then concentrated to obtain white solids. The solids are triturated with hot toluene and filtered. The filtrate upon cooling and addition of petroleum ether, yields 2-hydroxymethyl-5-chloroaniline m.p. 104-105. *The remaining solids are mostly unreacted 4-chloroanthranilic acid, which is only slightly soluble in toluene.

Reference： [1]Patent: US4164407,1979,A

5
[ 89-77-0 ]
[ 6625-94-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 478 - 483
Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 802 - 807
[2]Patent: DE931845,1952,
[3]Journal of the Chemical Society,1948,p. 1759,1765
[4]Journal of Medicinal Chemistry,2014,vol. 57,p. 3075 - 3093
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 5141 - 5156
[6]Journal of Medicinal Chemistry,2016,vol. 59,p. 7268 - 7274
[7]RSC Advances,2017,vol. 7,p. 22360 - 22368
[8]ACS Infectious Diseases,2019

6
[ 89-77-0 ]
[ 1499-21-4 ]
[ 5900-59-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonium hydroxide; triethylamine; In dichloromethane;	Reference example 1: 2-amino-4-chlorobenzamide 4-Chloroanthranilic acid (75 g, 0.437 mol) was suspended in dichloromethane (1.09 1). To this suspension, triethylamine (73 ml, 0.524 mol) and diphenylphosphoryl chloride (141 g, 0.524 mol) were added successively, and the mixture was stirred at room temperature for 1 hour. Then, 28percent aqueous ammonia (44 ml) was added, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was filtrated, the filtrated crude crystal was washed with methanol to give 51.0 g (yield 68percent) of the title compound as yellow crystal.

Reference： [1]Patent: EP1229025,2002,A1

7
[ 89-77-0 ]
[ 5900-59-4 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a solution of 2-amino-4-chlorobenzoic acid 11 (3.4 g,20 mmol) and HOBt (3.0 g, 22 mmol) in DMF (50 mL) was addedEDCI (4.6 g, 24 mmol). The mixture was stirred at rt for 2 h. Theresulting solution was cooled to 0 C, then 25% ammonia solution(20 mL) was added. The mixture was warmed to ambient temperatureand stirred for 1 h. The reaction mixture was poured intocrushed ice, filtered and washed with water to give 12 (3.0 g, 88%yield) as gray solid. 1H NMR (400 MHz, DMSO-d6) delta: 7.77 (s, 1H),7.54 (d, J = 8.5 Hz, 1H), 7.14 (s, 1H), 6.82 (s, 2H), 6.74 (d, J = 2.1 Hz,1H), 6.49 (dd, J = 8.5, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) delta:170.90, 151.98, 136.78, 131.06, 115.55, 114.45, 112.86 ppm. MS(ESI APCI) m/z 171.0 [M+H]+.
87.6%		Method I: 2-Amino-4-chlorobenzamide (ii-b) To a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL) was added HOBt (2.70 g, 20 mmol). After stirring for 10 min, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulted mixture was stirred at room temperature for 2 h. NH4OH (28%, 5 mL) was added at 0 C. with vigorous stirring. After addition, the mixture was stirred at room temperature for another 2 h. The reaction mixture was added to water (200 mL) dropwise with stirring, then a precipitate formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a grey solid (87.6% yield). LCMS m/z=171.0 (M+1), 173.0 (M+3) (Method B) (retention time=1.39 min). 1H NMR (400 MHz, DMSO-d6): delta 7.27 (d, J=9.6 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 6.60 (dd, J=8.4, 2.0 Hz, 1H), 5.50-5.82 (m, 4H).
87.6%		HOBt (2.70 g, 20 mmol) was added to a mixture of 2-amino-4-chlorobenzoic acid (3.42 g, 20 mmol) in DMF (45 mL).After stirring for 10 minutes, EDC hydrogen chloride (3.82 g, 20 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 2 hours.NH 4 OH (28%, 5 mL) was added at 0 C. with vigorous stirring.After the addition, the mixture was stirred at room temperature for a further 2 hours.The reaction mixture was added dropwise to water (200 mL) with stirring, and a precipitate was formed. The precipitate was collected and dried in vacuo to give 2.98 g of ii-b as a gray solid (yield 87.6%).

66%

With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃; for 96h;

[00393] Step A: To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NH3MeOH (18 mL, 36 mmol), and the solution was stirred at rt for 4 d. The mixture was concentrated under reduced pressure and the residue was partitioned between H2O (200 mL) and DCM (200 mL). The separated aqueous phase was extracted with DCM (2 X 200 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-50% EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 660Zo)-1H NMR (300 MHz, DMSO-J6) delta 6.50 (dd, J= 8.48, 2.26 Hz, 1 H), 6.75 (d, J = 2.26 Hz, 1 H), 6.84 (br s, 2 H), 7.18 (br s, 1 H), 7.48 - 7.63 (m, 1 H), 7.80 (br s, 1 H).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 1361 - 1375
[2]Patent: US2015/307477,2015,A1 .Location in patent: Paragraph 1473
[3]Patent: JP6121658,2017,B2 .Location in patent: Paragraph 1063; 1064; 1065
[4]Patent: WO2010/99379,2010,A1 .Location in patent: Page/Page column 142
[5]ARKIVOC,2012,vol. 2012,p. 198 - 213
[6]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 6883 - 6889
[7]Biochemistry,2017,vol. 56,p. 6491 - 6502
[8]Chinese Chemical Letters,2019,vol. 30,p. 1207 - 1213
[9]Phosphorus, Sulfur and Silicon and the Related Elements,2019

8
NH₃/MeOH [ No CAS ]
[ 89-77-0 ]
[ 5900-59-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With DIEA; benzotriazol-1-ol; In N,N-dimethyl-formamide;	Step A:To solution of 2-amino-4-chlorobenzoic acid (4.4 g, 25.8 mmol) in degassed DMF (75 mL) were added successively HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.37 g, 28 mmol), and 2N NH3/MeOH (18 mL, 36 mmol), and the solution was stirred at room temperature for 4 days.The mixture was concentrated under reduced pressure and the residue was partitioned between H2O (200 mL) and DCM (200 mL).The separated aqueous phase was extracted with DCM (2*200 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel chromatography eluting with 10-50percent EtOAc/hexanes to afford 2-amino-4-chlorobenzamide as a solid (2.91 g, 66percent).1H NMR (300 MHz, DMSO-d6) 86.50 (dd, J=8.48, 2.26 Hz, 1H), 6.75 (d, J=2.26 Hz, 1H), 6.84 (br s, 2H), 7.18 (br s, 1 H), 7.48-7.63 (m, 1H), 7.80 (br s, 1H).

Reference： [1]Patent: US2012/53176,2012,A1

9
[ 89-77-0 ]
[ 53449-14-2 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 4096 - 4109
[2]Patent: CN103570738,2016,B
[3]Patent: CN103382182,2016,B
[4]Patent: US2009/111772,2009,A1
[5]European Journal of Medicinal Chemistry,2018,vol. 147,p. 227 - 237
[6]Patent: CN108484574,2018,A

10
[ 59046-72-9 ]
[ 89-77-0 ]
4-chloro-17-iodo-18-phenyl-9-oxa-1-azatetracyclo[8.8.0.0^2,7.0^11,16]octadeca-2,4,6,11,13,15,17-heptaen-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine; sodium hydrogencarbonate; sodium sulfate; In acetonitrile; at 20℃; for 5h;	General procedure: To a stirred mixture of 1aA (0.42 g, 2.0 mmol) and 2a (0.279 g, 2.0 mmol) in MeCN (15 mL) were added NaHCO3 (0.252 g, 3.0 mmol), I2 (0.762 g, 3.0 mmol) and anhydrous Na2SO4 (0.289 g, 2.0 mmol) at room temperature. The reaction was allowed to proceed at room temperature until complete consumption of starting material as monitored by TLC (ca. 5 h). After the reaction was complete, the mixture was washed with saturated Na2S2O3 solution, extracted with EtOAc (2×25 mL), dried over anhydrous Na2SO4, and evaporated in vacuum on a rotary evaporator to afford a residue. This residue was purified by column chromatography on silica gel using hexanes-EtOAc (70:30, v/v) as the eluent to furnish 0.85 g (94%) of 3aAa as a white solid. 4.2.5 4-Chloro-17-iodo-18-phenyl-9-oxa-1-azatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6,11,13,15,17-heptaen-8-one (3aAe) Yield: 90% (0.87 g from 0.42 g) as a white solid, mp: 198-200 C; Rf=0.65 (CH2Cl2-MeOH, 9.5:0.5, v/v); IR (KBr) ν: 1725, 1591, 1424, 1262, 1088, 705 cm-1. 1H NMR (300 MHz, CDCl3): δ (ppm)=6.43 (d, 1H, J=1.1 Hz, ArH), 6.93 (s, 1H, CH), 7.12-7.15 (m, 3H, ArH), 7.34-7.45 (m, 5H, ArH), 7.59 (t, 1H, J=7.2 Hz, ArH), 7.76 (d, 1H, J=7.9 Hz, ArH), 7.98 (d, 1H, J=8.4 Hz, ArH); 13C NMR (75 MHz, CDCl3): δ (ppm)=90.2, 121.6, 122.7(2C), 126.7, 128.3, 128.6(4C), 130.5(2C), 131.2, 131.7(2C), 133.2, 138.2, 139.2, 139.4, 141.7, 144.8, 162.7. MS (ESI+): m/z=486.1. ESI-HRMS calculated for C22H13ClINO2 [MH]+: 485.9758, found: 485.9740. The details of the crystal structure investigation of this compound can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK vide CCDC no. 956063.

Reference： [1]Tetrahedron,2013,vol. 69,p. 9875 - 9885

11
[ 89-77-0 ]
[ 55496-69-0 ]

Reference： [1]Patent: CN103382182,2016,B
[2]Patent: US2009/111772,2009,A1

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Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Passerini Reaction ? Petasis Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

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[ 89-77-0 ]

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[ 20776-62-9 ]

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Chlorides

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Amines

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Carboxylic Acids

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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