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ChemicalBook CAS DataBase List 2-Chloro-5-methylpyridine-3-carboxylic acid
66909-30-6

2-Chloro-5-methylpyridine-3-carboxylic acid synthesis

4synthesis methods
2-CHLORO-5-METHYL-NICOTINIC ACID METHYL ESTER

65169-43-9

2-Chloro-5-methylpyridine-3-carboxylic acid

66909-30-6

General procedure for the synthesis of 2-chloro-5-methylnicotinic acid from 2-chloro-5-methylnicotinic acid methyl ester: Intermediate 31 (2-chloro-5-methylnicotinic acid methyl ester, 0.38 g, 1.81 mmol) was dissolved in methanol (2 ml) and 2N sodium hydroxide solution (1.81 ml, 3.62 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated to dryness and the residue was redissolved in ethyl acetate/water. The organic layer was separated, dried over magnesium sulfate and subsequently concentrated in vacuum to afford the target product 2-chloro-5-methylnicotinic acid as a white solid in 94% yield.LRMS: m/z 172 (M + 1)+; retention time: 3.25 min.1H NMR (200 MHz, DMSO-D6) δppm: 2.2 (s, 3H); 7.6 (d, J = 2.53 Hz , 1H); 8.0 (d, J = 2.53 Hz, 1H).

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Yield: 94%

Reaction Conditions:

with methanol;sodium hydroxide;water at 20; for 2 h;

Steps:

32
INTERMEDIATE 322-Chloro-5-methylnicotinic acid; Intermediate 31 (0.38g, 1.81mmol) was dissolved in MeOH (2ml) and 2N NaOH solution was added (1.81ml, 3.62mmol) and the mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue redissolved in EtOAc/ water. The organic layer was separated, dried over magnesium sulphate and concentrated in vacuum to yield the desired product as a white solid. Yield=94% LRMS: m/z 172 (M+1 )+ Retention time: 3.25min 1H NMR (200 MHz, DMSO-D6) δ ppm: 2.2 (s, 3 H); 7.6 (d, ?7=2.53 Hz, 1 H); 8.0 (d, J=2.53 Hz, 1 H)

References:

LABORATORIOS ALMIRALL, S.A. WO2008/77639, 2008, A1 Location in patent:Page/Page column 26-27

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