Ethyl 2-chloro-5-Methylnicotinate

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Ethyl 2-chloro-5-Methylnicotinate Basic information
Product Name:Ethyl 2-chloro-5-Methylnicotinate
Synonyms:Ethyl 2-chloro-5-Methylnicotinate;3-Pyridinecarboxylic acid, 2-chloro-5-methyl-, ethyl ester;ethyl 2-chloro-5-methyl-pyridine-3-carboxylate
CAS:894074-85-2
MF:C9H10ClNO2
MW:199.63
EINECS:
Product Categories:
Mol File:894074-85-2.mol
Ethyl 2-chloro-5-Methylnicotinate Structure
Ethyl 2-chloro-5-Methylnicotinate Chemical Properties
Boiling point 285.7±35.0 °C(Predicted)
density 1+-.0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-0.92±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Ethyl 2-chloro-5-Methylnicotinate Usage And Synthesis
Synthesis
Ethanol

64-17-5

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

66909-30-6

Ethyl 2-chloro-5-Methylnicotinate

894074-85-2

General procedure for the synthesis of ethyl 2-chloro-5-methylnicotinate from ethanol and 2-chloro-5-methylnicotinic acid: to a solution of 2-chloro-5-methylnicotinic acid (3.90 g, 22.7 mmol) in dichloromethane (DCM, 100 mL) was added oxaloyl chloride (9.95 mL, 114 mmol) followed by 1 drop of N,N-dimethylformamide (DMF). The reaction mixture was stirred at room temperature for 30 min, followed by evaporation of the solvent under vacuum. The resulting residue was dissolved in ethanol (EtOH, 66 mL) and stirring was continued for 2 h, after which the solvent was again evaporated under vacuum. The crude product was purified by fast column chromatography (silica gel SiO2, 120 g, eluent was a gradient solution of 0-50% dichloromethane in isohexane) to afford the target compound ethyl 2-chloro-5-methylnicotinate as a colorless oil (3.71 g, 82% yield).1H NMR (δ): 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H , q), 8.06-8.07 (1H, m), 8.41-8.43 (1H, m). [Ref: Yamamoto S. et al, Bioorg. Med. Chem. 2012, 20, 422-434.]

References[1] Patent: WO2016/55791, 2016, A1. Location in patent: Page/Page column 12
[2] Patent: WO2017/175000, 2017, A1. Location in patent: Page/Page column 28
Ethyl 2-chloro-5-Methylnicotinate Preparation Products And Raw materials
Raw materials2-Pentenoic acid, 2-cyano-, ethyl ester, (2E)--->Ethanol-->2-Chloro-5-methylpyridine-3-carboxylic acid-->N,N-Dimethylformamide-->Oxalyl chloride-->Dichloromethane
Tag:Ethyl 2-chloro-5-Methylnicotinate(894074-85-2) Related Product Information
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