成人免费xx,国产又黄又湿又刺激不卡网站,成人性视频app菠萝网站,色天天天天

Home Cart 0 Sign in  

[ CAS No. 133627-45-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 133627-45-9
Chemical Structure| 133627-45-9
Structure of 133627-45-9 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 133627-45-9 ]

Related Doc. of [ 133627-45-9 ]

Alternatived Products of [ 133627-45-9 ]
Product Citations

Product Details of [ 133627-45-9 ]

CAS No. :133627-45-9 MDL No. :MFCD00673152
Formula : C6H7ClN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :UOBCYTOUXLAABU-UHFFFAOYSA-N
M.W : 142.59 Pubchem ID :2756387
Synonyms :

Calculated chemistry of [ 133627-45-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.62
TPSA : 38.91 ?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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 0.981 mg/ml ; 0.00688 mol/l
Class : Soluble
Log S (Ali) : -1.92
Solubility : 1.7 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.64
Solubility : 0.324 mg/ml ; 0.00227 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 133627-45-9 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 133627-45-9 ]

* 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.

  • Downstream synthetic route of [ 133627-45-9 ]

[ 133627-45-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 49609-84-9 ]
  • [ 133627-45-9 ]
  • [ 133627-46-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethyl acetate; at 75 - 80℃; for 14h;Product distribution / selectivity; Example-3: Preparation of 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3 -pyridine carboxamide (V) [utilizing ethyl acetate as solvent during acylation]2-Chloro nicotinic acid (1.33kg; 8.44moles) was added to toluene (S.Olitres) and thionyl chloride (0.75 litres; 10.42 moles) and dimethyl formamide (100ml; 0.18moles) were added and the mixture refluxed at 80C-90C till completion of reaction. The reaction mixture was concentrated under reduced pressure and cooled between 25C and 300C. Ethyl acetate (8.0 litres) was added to the mixture followed by potassium carbonate (2.0kg; 15.15 moles). 3-Amino-2-chloro-4-methyl pyridine of formula (IIotaI).was dissolved in ethyl acetate and added to the acid chloride (IV). The mixture was refluxed at 75C to 8O0C for 14 hours. The reaction mixture was concentrated after completion of the reaction and water (5.0 litres) was added. The reaction mass was cooled between 10-150C, filtered and dried between 600C and 700C under reduced pressure..Yield: 1.73 kg. % Yield: 87.80%. HPLC Purity: 99.9%.
With potassium carbonate; In toluene; at 75 - 80℃; for 14h;Product distribution / selectivity; Example-4: Preparation of 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3 -pyridine carboxamide (V) [utilizing toluene as solvent and potassium carbonate as inorganic base during acylation]2-Chloro nicotinic acid (1.33kg; 8.44moles) was added to toluene (5.01itres) and thionyl chloride (0.75 litres; 10.42 moles) and dimethyl formamide (100ml; 0.18moles) were added and the mixture refluxed at 800C -9O0C till completion of reaction. The reaction EPO <DP n="20"/>mixture was concentrated under reduced pressure and cooled between 25C and 300C. Toluene (8.0 litres) was added to the residue containing compound (IV), followed by addition of potassium carbonate (2.0kg; 15.15 moles). 3-Amino-2-chloro-4-methyl pyridine of formula (III) dissolved in toluene was added to the acid chloride (IV). The mixture was refluxed at 750C to 800C for 14 hours. The reaction mixture was concentrated after completion of the reaction and quenched with water (5.0 litres). The reaction mass was cooled between 10-150C and filtered.Yield: 1.73 kg. % Yield: 87.80%. HPLC Purity: 99.9%.
With triethylamine; In toluene; at 25 - 32℃;Product distribution / selectivity; Example-5: Preparation of 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3 -pyridine carboxamide (V) [utilizing toluene as solvent during acylation and triethyl amine as organic base]2-Chloro nicotinic acid (1.33kg; 8.44moles) was added to toluene (5.01itres) and thionyl chloride (0.75 litres; 10.42 moles) and dimethyl formamide (100ml; 0.18moles) were added and the mixture refluxed at 800C -9O0C till completion of reaction. The reaction mixture was concentrated under reduced pressure. Toluene (8.0 litres) was added to the mixture. 3-Amino-2-chloro-4-methyl pyridine of formula (III) dissolved in toluene was added to the acid chloride (IV) and triethyl amine was added to the reaction mixture to adjust pH. The mixture was stirred at 250C to 32C. Impurity formation up to 30-40% was formed in the reaction mixture, therefore, the reaction was not worked up for isolation of compound (V).
With pyridine; In 1,4-dioxane; cyclohexane; at 25 - 32℃; for 2.5h;Product distribution / selectivity; Example 6: Preparation of 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (V) [utilizing toluene as solvent during acylation and pyridine as organic base]2-Chloro nicotinic acid (41.5gms; 0.263moles) was added to toluene (125ml) and thionyl chloride (19ml; 0.26moles) and dimethyl formamide (2.5ml; 0.005moles) were added and the mixture refluxed at 800C -900C till completion of reaction. The reaction mixture was concentrated under reduced pressure and the residue diluted with dioxane (55ml). Pyridine (62.5ml; 0.77moles) was added to a mixture of 3-Amino-2-chloro-4-methyl pyridine of formula (111) stirred in cyclohexane (62.5ml). The acid chloride (IV) mixture in dioxane, EPO <DP n="21"/>was added to the mixture containing (III) and stirred for 2.5 hours at 25C to 32C. TLC monitoring of the reaction mixture showed lot of impurities. The solid separating out was filtered washed with cyclohexane. Compound (V) was dissolved in acetone (300ml), refiuxed, and concentrated to 50ml. The mixture was cooled between 5 and 100C, filtered and dried.Yield: 32gms % Yield: 64.9%.
With N,N-dimethyl-aniline; In toluene; at 25 - 40℃; for 2.5h;Product distribution / selectivity; Example 11: Preparation of 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (V) [utilizing toluene as solvent and N,N-dimethyl aniline as organic base during acylation]2-Chloro nicotinic acid (165.75gms; 1.057moles) was added to toluene (542gms) and thionyl chloride (56.40gms; 0.477moles) and dimethyl formamide (5.9gms; 0.080moles) were added and the mixture refluxed at 80C-90C till completion of reaction. The reaction mixture was concentrated under reduced pressure and the residue diluted with toluene (542gms). 3-Amino-2-chloro-4-methyl pyridine (125gms; 0.877moles) of formula (III) was added to the mixture containing compound of formula (IV) at ambient temperature followed by addition of N,N-dimethyl aniline (127.12gms; 1.05moles). The reaction mixture was stirred for 2.5 hours at 250C to 4O0C. After completion of reaction, the reaction mixture was cooled to ambient temperature and neutralized with 10% sodium carbonate solution to pH 7.0 to 7.5. The solid separating out was filtered, washed with toluene and dried. Yield: 220-230 gms % Yield: 89-93%. Purity: 99%
With pyridine; In 1,4-dioxane; cyclohexane; at 20℃; for 48h;Product distribution / selectivity; 2-Chloro-N-(2-chloro-4-methyl-pyridin-3-yl)-nicotinamide: The procedure is carried out as described in Hargrave J. Med. Chem. 1991, 34, 2231-2241, which is hereby incorporated by reference in its entirety. To a solution of <strong>[133627-45-9]3-amino-2-chloro-4-methylpyridine</strong> (18.2 mmol) in 6:1 cyclohexane-dioxane (6 mL), and pyridine (5.75 mL) is added a solution of 2-chloronicotinoyl chloride (12.8 mmol) in 1,4-dioxane (5 mL). The resulting mixture is stirred at ambient temperature for 48 hours and the precipitate is filtered and washed with water. The solid is taken up in ethanol (17.5 mL) and aqueous NaOH (0.1 N, 3.6 mL). The solution is then heated to reflux for 2 hours, cooled to ambient temperature and stirred overnight. The solvent is removed under vacuum and water (10 mL) is added to residue, with stirring. The mixture is cooled to 1OC and the crystalline product is filtered, washed with cold water and dried under vacuum to give the desired product, 2-chloro-N-(2-chloro-4-methyl-pyridin-3-yl)-nicotinamide.
With pyridine; In acetonitrile; at 20 - 45℃;Product distribution / selectivity; Step 3[00287] 2-Chloro-N-(2-chloro-4-methyl-pyridin-3-ylVnicotinamide: Pyridine (125 g, 1.58 mol, 1.10 equiv) was added to a solution of 2-chloro-4-methyl-pyridin-3-ylamine (204.6 g, 1.44 mol, 1.00 equiv) in acetonitrile (1500 ml) in a 2 liter 3 -necked round-bottom flask. 2- chloronicotinoyl chloride (270 g, 1.54 mol, 1.07 equiv) was added dropwise to the solution while maintaining the temperature at 20 C. The solution was allowed to react overnight while maintaining the temperature at 45 C in an oil bath. The solution was then diluted with water (2 L) and sodium carbonate was added till the pH of the solution reached 8. The solution was filtered, the filter cake was washed with water (100mLx3), and the filter cake was dissolved in tetrahydrofuran (3 L). The solution was decolorized by the addition of active carbon, and then filtered. The filtrate was then dried over sodium sulfate, concentrated in vacuo using a rotary evaporator. The product of 2-chloro-lambda/-(2-chloro-4-methyl-pyridin-3-yl) nicotinamide (32Og, purity: 94%, yield:79%) was obtained as a light red solid. The material was used in next step without further purification.

  • 2
  • [ 23056-39-5 ]
  • [ 133627-45-9 ]
YieldReaction ConditionsOperation in experiment
90.79% Example-1 : Preparation of 3-Aniino-2-chloro-4-methyl pyridine of formula (III)First method: Reduction with Iron in acetic acid.2-Chloro-3-nitro-4-methylpyridine (II; lOOOgm, 5.75moles), was dissolved in acetic acid(10 litres) and heated to 700C -8O0C. Iron (750gm, 13.42moles) was added and the temperature maintained at 700C to 8O0C. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residual mass was diluted with water (5 litres). The pH of the aqueous layer was adjusted between 8.0-8.5 by addition of aqueous sodium carbonate solution and organic layer was separated. The aqueous layer was washed with ethyl acetate (2 litres). The organic layer after optional charcoal treatment was concentrated under reduced pressure to give 3-Amino-2-chloro-4-methyl pyridine of formula (III).Yield: 750gm %Yield: 90.79% HPLC purity: 99.25%.
90.1 - 96.7% Example 12: Preparation of 3-Amino-2-chloro-4-methyl pyridine of formula (III)First method: Reduction of 2-chloro-3-nitro-4-methyl pyridine with Iron and hydrochloric acid in an aqueous medium.2-Chloro-3-nitro-4-methylpyridine (II; lOOgm, 0.579moles), was suspended in methanol (1000 ml). Hydrochloric acid (550ml; 15.06 moles ) was added to the mixture and heated to 65C. Iron (195gms, 3.49moles) was added and the temperature maintained at 65C. The reaction mixture was monitored by thin layered chromatography and after completion of reaction; the reaction mixture was cooled to ambient temperature. Ethyl acetate was EPO <DP n="24"/>added to the reaction mixture and stirred. The organic layer was separated and concentrated. 3-Amino-2-chloro-4-methyl pyridine of formula (III) thus obtained was dried.Yield: 74.4gms~79.9gms %Yield: 90.1-96.7% HPLC purity: 99%.
90.7 - 96.8% Example 10: Preparation of 3-Amino-2-chloro-4-methyl pyridine of formula (III)First method: Reduction of 2-chloro-3-nitro-4-methyl pyridine with Iron and phosphoric acid in an aqueous medium.2-Chloro-3-nitro-4-methylpyridine (II; 2000gm, 11.59moles), was suspended in water (20 litres). Orthophosphoric acid (4.545kg; 46,36 moles ) was added to the mixture and heated between 70C-80C. Iron (1813 gms, 32.45moles) was added and the temperature maintained at 700C to 800C. The reaction mixture was monitored by thin layered chromatography and after completion of reaction; the reaction mixture was cooled to ambient temperature. Ethyl acetate was added to the reaction mixture and stirred. The EPO <DP n="23"/>organic layer was separated and concentrated. Cyclohexane (3.116 kg) was added to the residue with stirring and the resulting mixture after stirring at 10-150C for 60 minutes was filtered, washed with cyclohexane and dried to give 3-Amino-2-chloro-4-methyl pyridine of formula (III). Yield: 15 OOgms to 1600gms %Yield: 90.7 to 96.8% HPLC purity: 99%.
72.60% With sodium dithionite; In methanol; water; at 70 - 80℃;Product distribution / selectivity; Example-2: Preparation of 3-Amino-2-chloro-4-methyl pyridine of formula (III) EPO <DP n="19"/>Second method: Reduction with sodium dithionite2-Chloro-3-nitro-4-methylpyridine (II; lOOgm, 0.575moles), was dissolved in methanol (1000 ml) and heated to 70C-80C. Sodium dithionite (300gm, 1.725moles) dissolved in water (1000 ml) was added gradually to the reaction mixture and the temperature maintained at 700C to 8O0C. After completion of reaction, the reaction mixture was concentrated under reduced pressure, residue extracted with ethyl acetate (1000 ml) and the separated organic layer was then concentrated under reduced pressure to give 3-Amino-2-chloro-4-methyl pyridine of formula (III). Yield: 60gm % Yield: 72.60%HPLC purity: 99.25%.

  • 3
  • [ 108-24-7 ]
  • [ 133627-45-9 ]
  • [ 76006-00-3 ]
  • 4
  • [ 3430-27-1 ]
  • [ 133627-45-9 ]
YieldReaction ConditionsOperation in experiment
83.2% First, 21.6 g of 3-amino-4-methylpyridine was added to the reaction kettle,In the cold water bath slowly dropping 72mL concentrated hydrochloric acid,Stirring to clarify after warming to 40 C, 30 ~ 60min slowly dropping 30mL 30% hydrogen peroxide, temperature control reaction 2h.After completion of the reaction, the system rhoEta = 3 was adjusted with 45% sodium hydroxide solution, extracted with trichloromethane, dried and removed to obtain the crude product. Recrystallization from petroleum ether or n-hexane gave white or pale yellow needle-like crystals of 2-chloro-3-amino-4-methylpyridine with a purity of 99.0%, a yield of 83.2%
78% Step 2[00286] 2-chloro-4-methyl-pyridin-3 -ylamine : A solution of 4-methylpyridin-3 -amine(200 g, 1.85 mol, 1.00 equiv) in concentrated hydrochloric acid (3 L) was placed in a 5 L 3- necked round-bottom flask. Hydrogen peroxide (30%) (210 g, 1.85 mol, 1.00 equiv) was added dropwise to the solution while maintaining the temperature at 20 C. The resulting solution was allowed to react overnight at ambient temperature. Saturated aqueous sodium carbonate was added to the solution, till a pH of 8 was reached. The solution was filtered, and the filter cake was washed with water (100 ml x3). The filter cake was dissolved in ethyl acetate (300OmL) and dried over sodium sulfate. The solution was filtered, and the filtrate was concentrated in vacuo <n="74"/>using a rotary evaporator. The product (204.6 g, purity: 90%, yield:78%) of 2-chloro-4-methyl- pyridin-3-ylamine was obtained as a light red solid. The material was used in next step without further purification.
With hydrogenchloride; sodium hydroxide; chlorine; In water; F) Preparation of 3-amino-2-chloro-4-methylpyridine STR16 3-Amino-4-methylpyridine (21.6g, 0.2 mole) was suspended in 75 ml of water at room temperature. The mixture was dissolved by the addition of 25 ml conc. hydrochloric acid. The solution was cooled to 20 C. and 15.6 g (0.22 mole) of chlorine gas was introduced through an inlet tube reaching below the surface of the reaction mixture over 25 minutes. The mixture was stirred under a nitrogen purge for an additional 30 minutes, then cooled to 10 C. and basified by the addition of 70 mL of a 12.5 N. sodium hydroxide solution. Additional water (100 mL) was added to maintain efficient agitation of the mixture. The precipitate was collected, washed with water and dried to give 14.5g of the title product. The aqueous phase was extracted with 3 times 100 mL of methylene chloride. The organic phases were washed with water, dried over magnesium sulfate, and concentrated to give an additional 9.4g, mp 62-64
23.9 g (84%) With hydrogenchloride; sodium hydroxide; chlorine; In water; F) Preparation of 3-Amino-2-Chloro-4-Methylpyridine STR16 3-Amino-4-methylpyridine (21.6 g, 0.2 mole) was suspended in 75 ml of water at room temperature. The mixture was dissolved by the addition of 25 ml conc. hydrochloric acid. The solution was cooled to 20 C. and 15.6 g (0.22 mole) of chlorine gas was introduced through an inlet tube reaching below the surface of the reaction mixture over 25 minutes. The mixture was stirred under a nitrogen purge for an additional 30 minutes, then cooled to 10 C. and basified by the addition of 70 mL of a 12.5 N. sodium hydroxide solution. Additional water (100 mL) was added to maintain efficient agitation of the mixture. The precipitate was collected, washed with water and dried to give 14.5 g of the title product. The aqueous phase was extracted with 3 times 100 mL of methylene chloride. The organic phases were washed with water, dried over magnesium sulfate, and concentrated to give an additional 9.4 g, mp 62-64 C. Total yield, 23.9 g (84%).
With hydrogenchloride; dihydrogen peroxide; In water; at 0 - 20℃; for 1h; 62c) 2-chloro-4-methylpyridin-3-amine A mixture of 4-methylpyridin-3-amine (0.62 g), 12N hydrogen chloride (3.8 mL) and 30% hydrogen peroxide (0.75 mL) was stirred at 0 C. to room temperature for 1 h. The mixture was neutralized with K2CO3, and the mixture was extracted with AcOEt. The organic layer was dried over MgSO4, and concentrated in vacuo to give 2-chloro-4-methylpyridin-3-amine (0.75 g) as an orange solid.MS (API+): [M+H]+ 143.1.

  • 5
  • [ 152362-01-1 ]
  • [ 133627-45-9 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hypobromide; bromine; sodium hydroxide; In water; at 65 - 75℃; for 4h; Bromine (1.6 g) was added to a solution of sodium hydroxide (1.6 g) in fresh water or sea water (11.8 g) at 0-5C. 2-Chloro-4-methyl nicotinamide (1.7 g) was added to cold sodium hypobromite solution in 1.5 h. The ice bath was removed, and the reaction mixture was allowed to warm to room temperature. The resulting yellow solution was heated to 65C for 2 h, and warmed to 75C for 2 h. When the solution cooled to room temperature, the product was extracted three times with chloroform (30 mL). The combined extract was dried over anhydrous sodium sulfate, filtered, and concentrated to a solid. Recrystallization with n-hexane yielded a coarse white crystal product. The product yield using zinc powder-treated sea water as raw material was 98%, mp 70-71C. (Literature [7]: Yield 92.3%, mp 69-70C). The synthesis route of 3-amino-2-chloro-4-methylpyridine is shown in Scheme 2.
96.9% With bromine; sodium hydroxide; In water; toluene; at 0 - 60℃; 1. COMAD (10,3 g) was added to a 3-neck flask fitted with a thermocouple, a dropping funnel, and a heating and cooling system.2. Water (15 g) was added to the reactor and the suspension was agitated.3. The mixture was cooled to 0-5C.4. The NaOBr solution of vessel I was added to the COMAD suspension in vessel 2 slowly while maintaining the temperature between 0-5C.5. Afier charging was complete, the temperature of the reaction mixture was held at0-5C for 15-20 minutes. A clear yellow solution resulted; no solid or suspension was formed.6. The reactor contents were allowed to warm to 15C and were held at this temperature for 15-20 minutes.7. The reaction mixture was heated to 25C and maintained at a temperature between22-25C for 1.5 hours, or until the evolution of heat subsided.8. 10 ml of water was added to the reaction mixture which was then heated to 80C and held for 1 hour.9. The reaction mixture was then cooled to 50-60C and toluene (21.62 g) was added; the mixture was agitated for 15-20 minutes.10. The top organic layer was separated.11. Toluene (10.3 g) was added to the aqueous layer and the mixture was agitated for15-20 minutes. The agitation was stopped and the top organic layer was separated.12. The organic layers were combined and washed with water (10 g) and the water layer was decanted.13. Toluene (25.0 g) was removed via distillation under reduced pressure.14. The reactor temperature was adjusted to 55-60C and hexane (6.5 g) was added slowly with agitation over 15 minutes. The solution because cloudy and a white precipitate started to appear.15. The mixture was cooled slowly to room temperature and then to 0-5C.16. The mixture was held at 0-5C for 1 hour.17. The solid precipitate was retrieved by filtered and washed once with hexanes (6.6 g).18. The product was dried under vacuo at 25C to a constant weight.In an exemplary synthesis, the isolated yield was 8.34 g (96.9%) of off white to white crystalline product.
90.6% With sodium hydroxide; bromine; In water; at 0 - 75℃; for 3h; Example 11 Synthesis of 3-amino-2-chloro-4-methylpyridine (1) A solution of 11.7g (0.293 mole) of sodium hydroxide in 11 ML of water was stirred and cooled to 0C. bromine 14.2g (0.293 mole) was added dropwise maintaining the temperature at 0C. To a pale yellow solution was added 13.2g (0.077 mole) of 2-Chloro-4-methylnicotinamide (10) in portions at 0-5C. The ice-bath was removed and the reaction mixture warmed to 75C over one hour and maintained at 60-75C for an additional 2 hours.. The mixture was cooled overnight and the crystalline product collected by filtration to give 10g (90.6%) of the title compound [mp: 62-64C]. NMR and MS was identical to data reported by Hargrave, et al., J. Heterocyclic Chem., 34, 223 (1991).
90.6% Example 6 Synthesis of 3-amino-2-chloro-4-methylpyridine (1) A solution of 11.7g (0.293 mole) of sodium hydroxide in 11 mL of water was stirred and cooled to 0C. Bromine 14.2g (0.293 mole) was added dropwise maintaining the temperature at '0C. To a pale yellow solution was added 13.2g (0.077 mole) of 2-chloro-4-methylpyridine-3-carboxamide (9) in portions at 0-5C. The ice-bath was removed and the reaction mixture warmed to 75C over one hour and maintained at 60-75C for an additional 2 hours. The mixture was cooled overnight and the crystalline product collected by filtration to give 10g (90.6%) of the title compound [mp: 62-64C]. NMR and MS was identical to data reported by Hargrave et al., J. Heterocyclic Chem., 34, 223 (1991).
10 g (90.6%) With sodium hydroxide; bromine; In water; EXAMPLE 6 Synthesis of 3-amino-2-chloro-4-methylpyridine (1) A solution of 11.7 g (0.293 mole) of sodium hydroxide in 11 mL of water was stirred and cooled to 0 C. Bromine 14.2 g (0.293 mole) was added dropwise maintaining the temperature at 0 C. To a pale yellow solution was added 13.2 g (0.077 mole) of 2-chloro-4-methylpyridine-3-carboxamide (9) in portions at 0-5 C. The ice-bath was removed and the reaction mixture warmed to 75 C. over one hour and maintained at 60-75 C. for an additional 2 hours. The mixture was cooled overnight and the crystalline product collected by filtration to give 10 g (90.6%) of the title compound [mp: 62-64 C.]. NMR and MS was identical to data reported by Hargrave et al., J. Heterocyclic Chem., 34, 223 (1991).
41.5 g With calcium hypochlorite; calcium oxide; In water; at 10℃; To the above mixture, 61.5 g of calcium hypochlorite was added in portions,After the addition was complete, the heat was kept stirring for 30 minutes,50 mL of an aqueous solution of 40 wt% calcium oxide was further added in portions,Control temperature does not exceed 10 ,The reaction was continued for 2 to 3 hours to obtain a reaction mixture.The resulting cold reaction mixture was added dropwise to water (150 mL)Control temperature of 100 degrees or less; dropping finished,70 ~ 80 C to continue the reaction 2 hours; cooling to 5 C,With concentrated hydrochloric acid adjusted pH value of 6.5 to 7; suction filtration,The filter cake was washed with ice water; the filter cake was added to 75 mL of water,Heated to 60 to 70 C, stirred for 30 minutes,Slowly cooled to 0 ~ 5 , the precipitation of crystals, filtration,The filter cake was washed with ice water, dried in vacuo,To obtain 41.5 g of 2-chloro-3-amino-4-methylpyridine,HPLC purity was 99.9%.

  • 7
  • [ 133627-45-9 ]
  • (Z)-ethyl 3-(2-chloro-4-methylpyridin-3-ylamino)-2-cyano-3-isopropylaminoacrylate [ No CAS ]
  • 8
  • [ 133627-45-9 ]
  • (Z)-ethyl 3-(2-chloro-4-methylpyridin-3-ylamino)-3-propylamino-2-cyanoacrylate [ No CAS ]
  • 9
  • [ 133627-45-9 ]
  • (Z)-ethyl 3-butylamino-3-(2-chloro-4-methylpyridin-3-ylamino)-2-cyanoacrylate [ No CAS ]
  • 10
  • [ 133627-45-9 ]
  • (Z)-ethyl 3-benzylamino-3-(2-chloro-4-methylpyridin-3-ylamino)-2-cyanoacrylate [ No CAS ]
Recommend Products
Same Skeleton Products

Technical Information

Historical Records

Related Functional Groups of
[ 133627-45-9 ]

Chlorides

Chemical Structure| 357263-41-3

[ 357263-41-3 ]

7-Chloro-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.83

Chemical Structure| 342899-38-1

[ 342899-38-1 ]

3-Chloroisoquinolin-4-amine

Similarity: 0.83

Chemical Structure| 39745-40-9

[ 39745-40-9 ]

3-Amino-2-chloro-6-picoline

Similarity: 0.81

Chemical Structure| 342899-34-7

[ 342899-34-7 ]

3-Amino-2-chloroisonicotinamide

Similarity: 0.79

Chemical Structure| 58142-49-7

[ 58142-49-7 ]

3-Chloroisoquinolin-5-amine

Similarity: 0.78

Amines

Chemical Structure| 342899-38-1

[ 342899-38-1 ]

3-Chloroisoquinolin-4-amine

Similarity: 0.83

Chemical Structure| 39745-40-9

[ 39745-40-9 ]

3-Amino-2-chloro-6-picoline

Similarity: 0.81

Chemical Structure| 342899-34-7

[ 342899-34-7 ]

3-Amino-2-chloroisonicotinamide

Similarity: 0.79

Chemical Structure| 58142-49-7

[ 58142-49-7 ]

3-Chloroisoquinolin-5-amine

Similarity: 0.78

Chemical Structure| 51564-92-2

[ 51564-92-2 ]

6-Chloro-4-methylpyridin-2-amine

Similarity: 0.76

Related Parent Nucleus of
[ 133627-45-9 ]

Pyridines

Chemical Structure| 39745-40-9

[ 39745-40-9 ]

3-Amino-2-chloro-6-picoline

Similarity: 0.81

Chemical Structure| 342899-34-7

[ 342899-34-7 ]

3-Amino-2-chloroisonicotinamide

Similarity: 0.79

Chemical Structure| 51564-92-2

[ 51564-92-2 ]

6-Chloro-4-methylpyridin-2-amine

Similarity: 0.76

Chemical Structure| 97004-04-1

[ 97004-04-1 ]

(6-Chloropyridin-3-yl)methanamine

Similarity: 0.73

Chemical Structure| 66909-38-4

[ 66909-38-4 ]

6-Chloro-4-methylpyridin-3-amine

Similarity: 0.72

; ;