[ CAS No. 614-18-6 ] {[proInfo.proName]}

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Quality Control of [ 614-18-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 614-18-6 ]

SDS Specification

Alternatived Products of [ 614-18-6 ]

Product Details of [ 614-18-6 ]

CAS No. :	614-18-6	MDL No. :	MFCD00006389
Formula :	C₈H₉NO₂	Boiling Point :	-
Linear Structure Formula :	CH₃CH₂OC(O)C₅H₄N	InChI Key :	XBLVHTDFJBKJLG-UHFFFAOYSA-N
M.W :	151.16	Pubchem ID :	69188
Synonyms :

Calculated chemistry of [ 614-18-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.32
TPSA :	39.19 ?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) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.26
Log Po/w (MLOGP) :	0.66
Log Po/w (SILICOS-IT) :	1.51
Consensus Log Po/w :	1.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.81
Solubility :	2.32 mg/ml ; 0.0153 mol/l
Class :	Very soluble
Log S (Ali) :	-1.74
Solubility :	2.73 mg/ml ; 0.018 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.491 mg/ml ; 0.00325 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 614-18-6 ]

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 [ 614-18-6 ]

* 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 [ 614-18-6 ]
Downstream synthetic route of [ 614-18-6 ]

[ 614-18-6 ] Synthesis Path-Upstream 1~1

1
[ 614-18-6 ]
[ 1762-46-5 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 9, p. 3013 - 3014
[2] Journal of the American Chemical Society, 1987, vol. 109, # 22, p. 6619 - 6626
[3] Angewandte Chemie, 1986, vol. 98, # 12, p. 1119 - 1121
[4] Dalton Transactions, 2011, vol. 40, # 21, p. 5706 - 5710
[5] Journal of the Chemical Society, 1956, p. 616,619
[6] Journal of the Chemical Society, 1961, p. 1347,1349

[ 614-18-6 ] Synthesis Path-Downstream 1~11

1
[ 614-18-6 ]
[ 141-78-6 ]
[ 6283-81-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium ethanolate; for 16h;Heating / reflux;	(1). Sodium (38 g, 1.65 mol) was slowly added to 900 mL of ethanol and left to stir at RT for 4 h. Solvent was removed in vacuo. Ethyl acetate (200 mL) was addded to the sodium ethoxide followed by ethyl nicotinate (22.6 mL, 0.166 mol) in 150 mL of ethyl acetate. The reaction was heated to reflux for 16 h. Water (200 mL) was added to the reaction mixture. The aqueous layer was acidified to pH 6 with HCl and extracted with ether. Solvent was removed in vacuo to give a brown oil which was purified by column chromatography (2:1, hexanes-EtOAc), to give 1 (101 g, 52%).
37.1%	With lithium tert-butoxide; for 4h;Reflux;	Add 10 ml of ethyl acetate to a 25 ml round bottom flask.Ethyl nicotinate 1.0g,Lithium tert-butoxide 0.794g,The reaction was refluxed for 4 hours, and the reaction was completed by TLC. The reaction mixture was cooled to room temperature, and 60 ml of 3M HCl solution was added thereto and stirred for 5 minutes. Then, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (90 ml). Dry over sodium sulfate, filter, concentrate,The compound 3-oxo-(3-pyridyl)propionic acid ethyl ester is obtained.The colorless oil was 0.474 g, and the yield was 37.1%.
3 g	With sodium ethanolate; for 20h;Reflux;	Ethyl 3-picolinate (2.5 g, 16 mmol) was weighed out in a 250 mL eggplant flask,Followed by 60 mL of EA,NaOEt 12 g (176 mmol),Heated to reflux after 20h to stop the reaction,Was removed by rotary evaporation EA, with 2mol / L HCl adjusted to pH 8-9, 3 times (3 × 40mL), the combined organic phase was extracted with EA, dried over anhydrous Na2SO4, separation and purification by column chromatography (petroleum ether / ethyl acetate = 3/ 1) to give 3 g of a yellow oily liquid which was used directly in the next step.

Reference： [1]Patent: US2004/116425,2004,A1 .Location in patent: Page 86
[2]ChemMedChem,2010,vol. 5,p. 1373 - 1385
[3]Patent: CN110156761,2019,A .Location in patent: Paragraph 0038; 0081-0082
[4]Journal of the American Chemical Society,1927,vol. 49,p. 557
[5]Journal of the American Chemical Society,1948,vol. 70,p. 2755,2757
[6]Patent: CN106674176,2017,A .Location in patent: Paragraph 0129; 0130

2
[ 614-18-6 ]
[ 5166-67-6 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 3831

3
[ 614-18-6 ]
[ 141-43-5 ]
[ 6265-73-2 ]

Yield	Reaction Conditions	Operation in experiment
96.6%		(A) A mixture of 1.6 kg of ethyl nicotinate,Ethanolamine 1.1kg into the reactor.The reaction was heated to 125 C for 4 hours.After completion of the reaction,Cooled to 100 C,Vacuum distillation,Vacuum distillation vacuum-0.091MPa distillation temperature rose to 130 ~ 135 when the end of distillation, the reaction solution;(B) The reaction solution can be rapidly cooled to 80 C with brine under stirring,And then slowly cooled to 65 ;(C) 1.6 kg of acetone was added dropwise at 60 C,After the dropwise addition was continued, the temperature was gradually lowered to 45 C,Crystal precipitation,And the mixture was stirred at 45 C for 1 hour.(D) continue to cool to 30 C,Stir for 1.5 hours,And then continue to cool to 10-15 ,Stirred for 1 hour,And then continue to cool to 0 or so,Stirring crystallization after 1 hour out.Centrifugation,The filter cake,The oven was dried at 50-60 & lt; 0 & gt; C,To obtain 1.70 kg of white N- (2-hydroxyethyl) -nicotinamide,The overall yield was 96.6%Mp 89-91 C.
64.5%		EXAMPLE 91 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A neat mixture of 2-aminoethanol (6.1 g, 0.10 mol) and ethyl nicotinate (15.1 g, 0.10 mol) was refluxed overnight. As the mixture was cooled to room temperature, the product precipitated as a crystalline solid. It was filtered, washed with ether and then recrystallized from 2-propanol/ether. The final productproduct was collected by vacuum filtration and washed with ether. The dried, white compound weighed 10.7 g, resulting in a 64.5% yield; mp 88.5-89.5 C. (lit. value 92 C.).
64.5%		EXAMPLE 91 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A neat mixture of 2-aminoethanol (6.1 g, 0.10 mol) and ethyl nicotinate (15.1 g, 0.10 mol) was refluxed overnight. As the mixture was cooled to room temperature, the product precipitated as a crystalline solid. It was filtered, washed with ether and then recrystallized from 2-propanol/ether. The final productproduct was collected by vacuum filtration and washed with ether. The dried, white compound weighed 10.7 g, resulting in a 64.5% yield; mp 88.5-89.5 C. (lit. value 92 C).

64%	at 20 - 55℃; for 18h;	General procedure: For the synthesis of the hydroxylated precursors, ethanolamine (1.5 mmol) was added slowly to the esters (1 mmol) at 55C and stirred for 3 h. The reaction mixture was stirred at room temperature for 15 h. The residue was purified by silica gel column chromatography (eluent/ethyl acetate/hexane 8:2) or recrystallized from ethyl acetate. The progress of the reaction was monitored by TLC.`
42%	In toluene; at 80℃; for 48h;	Ethyl nicotinate (15.1 g, 100.0 mmol, 1.0 eq.) and Ethanolamine (6.1 g, 100.0 rnrnol, 1.0 eq.) were dissolved in toluene (80 ml_). The reaction mixture was heated to 80 0C and stirred for 48 h. During the reaction the mixture changed into a sticky emulsion. The emulsion was cooled down to room temperature and the lower phase became solid. The upper liquid phase was decanted and the orange solid was crystallised twice, first from ethyl acetate and then from acetone. The crystals were dried under high vacuum at room temperature to give 7.1 g (42 %) of the product as a white, free flowing powder. The 1 H NMR and the 13C NMR corresponds to the literature (Ogawa, T.; Hatayama, K.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1994, 42 (8) 1579-1589). 1H NMR (CDCI3) delta = 3.60-3.64 (q, 2H), 3.82-3.85 (t, 2H), 4.00 (s, 1H), 7.33-7.39 (m, 2H), 8.10-8.14 (m, 1H), 8.64-8.67 (q, 1 H)1 8.99-9.00 (t, 1 H). 13C NMR (CDCI3) delta = 42.8, 61.5, 123.6, 130.2, 135.5, 147.8, 152.0, 166.4.
		EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours. The resulting white solid was removed by filtration, affording 46 g (85.1%) of the title compound melting at 75-78 C.
		EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours The resulting white solid was removed by filtration, affording 46 g 15 (85 1%) of the title compound melting at 75-78 C.

Reference： [1]Patent: CN105218441,2016,A .Location in patent: Paragraph 0069; 0070; 0071; 0072; 0073
[2]Patent: US4983586,1991,A
[3]Patent: US5017566,1991,A
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2783 - 2790
[5]Patent: WO2007/39059,2007,A1 .Location in patent: Page/Page column 23
[6]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455
[7]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 808 - 816
[8]Patent: US4983586,1991,A
[9]Patent: US5017566,1991,A
[10]Organic Letters,2016,vol. 18,p. 3434 - 3437

4
[ 614-18-6 ]
[ 151-50-8 ]
[ 76196-79-7 ]

Reference： [1]Synthesis,2005,p. 993 - 997

5
[ 614-18-6 ]
[ 326-62-5 ]
2-(2-fluoro-phenyl)-1-pyridin-3-yl-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure D for the Synthesis of Fluoroethyl Aryl Pyridinyl Substituted Ethyl Ureas: An (iso)nicotinic acid ethyl ester and a substituted phenyl acetonitrile (1:1 ratio) were dissolved in EtOH (100 mL), then sodium ethoxide (21% in EtOH, 1.0 eq was added. The resulting reaction mixture was refluxed for 3 hours, then cooled to 0 C., concentrated HCl was added to adjust the acidity to pH=3. A solid, presumably the intermediate cyanoketone, was formed and filtered. The solid was then washed with water and dried under house vacuum. This cyanoketone was mixed with 48% hydrobromic acid (80 mL) and the mixture was refluxed for 5 hours. After cooling to room temperature, the reaction mixture was basified with ammonium hydroxide, and then extracted with ethyl acetate. The combined organic phases were washed with brine, then dried with magnesium sulfate and concentrated to give the desired diaryl ketone42. This ketone was then converted into the desired amine via oxime intermediate according to the protocol described in general procedure B. The final fluoroethyl urea was thus obtained using this amine and fluoroethyl ammonium chloride according to general procedure A. 42 Clader, John W.; Berger, Joel G.; Burrier, Robert E.; Davis, Harry R.; Domalski, Martin; et al. J. Med. Chem. 1995, 38, 1600-1607. The title ketone was obtained from nicotinic acid ethyl ester (10.00 g, 66.16 mmol), (2-fluoro-phenyl)-acetonitrile (9.12 g, 67.49 mmol), sodium ethoxide (50.00 mL, 21 wt. % in EtOH, 0.13 mol) and hydrobromic acid (48%, 80.00 mL) according to the protocols as outlined in general procedure D described above. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) delta ppm 4.53 (s, 2H) 7.10-7.23 (m, 2H) 7.24-7.36 (m, 2H) 7.58 (dd, J=7.92, 5.57 Hz, 1H) 8.36 (dt, J=8.14, 1.94 Hz, 1H) 8.81 (dd, J=4.84, 1.61 Hz, 1H) 9.22 (d, J=1.47 Hz, 1H).

Reference： [1]Patent: US2007/270498,2007,A1 .Location in patent: Page/Page column 21-22

6
[ 614-18-6 ]
[ 194726-40-4 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 4343 - 4347

7
[ 14062-24-9 ]
[ 614-18-6 ]
[ 14062-29-4 ]
[ 40061-24-3 ]

Yield	Reaction Conditions	Operation in experiment
		p-xylyl-(3-pyridyl)-ketone, m.p. 90-91C (from ether), starting from 21.0 g of p-tolylacetic acid ethyl ester and 17.8 g of nicotinic acid ethyl ester; m-chlorobenzyl-(3-pyridyl)-ketone, m.p. 65-67C, starting from 25.0 g of m-chlorophenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester; p-chlorobenzyl-(3-pyridyl)-ketone (oil), starting from 25.0 g of p-chlorophenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester; p-methoxybenzyl(4-pyridyl)-ketone, m.p. 130-132C, starting from 25.2 g of p-methoxyphenylacetic acid ethyl ester and 18.9 g of nicotinic acid ethyl ester; m-methoxybenzyl-(3-pyridyl)-ketone, b.p. 160-165C/0.05 Torr, starting from 25.2 g of m-methoxyphenylacetic acid ethyl ester and 19.0 g of nicotinic acid ethyl ester.

Reference： [1]Patent: US3940486,1976,A

8
[ 614-18-6 ]
[ 141-78-6 ]
[ 6283-81-4 ]
[ 141-97-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With lithium hexamethyldisilazane; In tetrahydrofuran; at -40℃; for 0.333333h;Inert atmosphere;	General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4193 - 4197

9
[ 614-18-6 ]
[ 697739-12-1 ]

Reference： [1]Patent: US2015/344483,2015,A1
[2]Patent: WO2013/102142,2013,A1

10
[ 614-18-6 ]
[ 76196-79-7 ]

Reference： [1]Patent: WO2013/102142,2013,A1

11
[ 614-18-6 ]
[ 76196-79-7 ]
[ 75358-90-6 ]

Reference： [1]Patent: WO2013/102145,2013,A1
[2]Patent: US2015/344483,2015,A1

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Technical Information

? Acyl Group Substitution ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Preparation of Amines ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents

Historical Records

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[ 614-18-6 ]

Esters

[ 94-44-0 ]

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[ 614-18-6 ]

Pyridines

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Benzyl nicotinate

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Ethyl 5-methylnicotinate

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Tetradecyl pyridine-3-carboxylate

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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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[ CAS No. 614-18-6 ] {[proInfo.proName]}

Quality Control of [ 614-18-6 ]

Related Doc. of [ 614-18-6 ]

Product Details of [ 614-18-6 ]

Calculated chemistry of [ 614-18-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 614-18-6 ]

Application In Synthesis of [ 614-18-6 ]

[ 614-18-6 ] Synthesis Path-Upstream 1~1

[ 614-18-6 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 614-18-6 ]

Esters

Related Parent Nucleus of [ 614-18-6 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 614-18-6 ]

Related Parent Nucleus of
[ 614-18-6 ]