ethyl 6-chloro-3-Methylpicolinate synthesis
- Product Name:ethyl 6-chloro-3-Methylpicolinate
- CAS Number:850864-54-9
- Molecular formula:C9H10ClNO2
- Molecular Weight:199.63
850864-53-8
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Yield:850864-54-9 86%
Reaction Conditions:
with N,N-dimethyl-formamide;trichlorophosphate in dichloromethane at 0 - 20;
Steps:
22.8.C Alternative synthesis of 3-[[6-[3-(hydroxymethyl)phenyl]-3-methyl-pyridine-2- carbonyllamino -2.4-dimethyl-benzoic acid (Example 22). Scheme 8. Step C.
Phosphorous oxychloride (1.16 L, 12.4 mol) is added dropwise at 0 °C over ~1 hour to a solution of DMF (2.45 L, 24.8 mol) and methylene chloride (4.5 L) The reaction is stirred for 30 minutes at 0 °C, then ethyl 3 -methyl- 1-oxido-pyridin-l- ium-2-carboxylate (450 g, 2.48 mol) is added. The reaction is allowed to slowly warm overnight to room temperature, and the reaction mixture is poured into ice water (10 L). The pH is adjusted with 10% sodium carbonate to pH~8, and the mixture is stirred for 1 hour. The layers are separated, and the aqueous layer is extracted with methylene chloride (2 x 2 L). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to give ethyl 6-chloro-3-methyl-pyridine-2- carboxylate as a beige semi solid (425 g, 86%). MS (m/z) 200 [M+H]+.
References:
WO2015/94912,2015,A1 Location in patent:Page/Page column 31
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