4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

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4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Basic information
Product Name:4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
Synonyms:ethyl 4-chloro-1,6-dihydro-1-Methyl-6-oxopyridine-3-carboxylate;3-Pyridinecarboxylicacid, 4-chloro-1,6-dihydro-1-Methyl-6-oxo-, ethyl ester; ethyl 4-chloro-1-methyl-6-oxopyridine-3-carboxylate;ETHYL 4-CHLORO-1-METHYL-6-OXO-1,6-DIHYDROPYRIDINE-3-CARBOXYLATE;4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
CAS:821791-58-6
MF:C9H10ClNO3
MW:215.63
EINECS:
Product Categories:
Mol File:821791-58-6.mol
4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Structure
4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Chemical Properties
Boiling point 302.4±42.0 °C(Predicted)
density 1.31±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka-3.05±0.62(Predicted)
AppearanceYellow to brown Solid
Safety Information
MSDS Information
4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Usage And Synthesis
Synthesis
4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

853105-37-0

4-CHLORO-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

821791-58-6

(Step 2) To ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (9.2 g, 47 mmol) obtained in Step 1 was added phosphorous trichloride (26.1 mL, 280 mmol) and triethylamine (6.5 mL, 47 mmol). The reaction mixture was stirred at 50 °C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. Saturated aqueous sodium bicarbonate (100 mL) was added to the residue, which was subsequently extracted with ethyl acetate (3 × 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6.0 g, 60% yield). The product was confirmed by electrospray ionization mass spectrometry (ESIMS), m/z: 216 (M + H)+.

References[1] Patent: EP2930170, 2015, A1. Location in patent: Paragraph 0253
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 441 - 444
[3] Patent: US2005/256123, 2005, A1
4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Preparation Products And Raw materials
Raw materialsEthyl 4,6-dichloronicotinate-->4-Hydroxy-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester-->Dimethyl sulfate
Preparation Products4-Chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
Tag:4-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester(821791-58-6) Related Product Information
3-Pyridinecarboxylic acid, 4-chloro-1,6-dihydro-1-methyl-6-oxo-, methyl ester 4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 4-Chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid 4,5-Dichloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester Ethyl 5-bromo-4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate 4-Chloro-5-fluoro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester