4-chloro-N-methoxy-N-methylpicolinamide

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4-chloro-N-methoxy-N-methylpicolinamide Basic information
Product Name:4-chloro-N-methoxy-N-methylpicolinamide
Synonyms:4-chloro-N-methoxy-N-methylpicolinamide;4-Chloro-N-methoxy-N-methylpyridine-2-carboxamide;2-Pyridinecarboxamide, 4-chloro-N-methoxy-N-methyl-;4-Chloro-N-methoxy-N-methyl-2-pyridinecarboxamide
CAS:757251-62-0
MF:C8H9ClN2O2
MW:200.62
EINECS:
Product Categories:
Mol File:757251-62-0.mol
4-chloro-N-methoxy-N-methylpicolinamide Structure
4-chloro-N-methoxy-N-methylpicolinamide Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
Safety Information
MSDS Information
4-chloro-N-methoxy-N-methylpicolinamide Usage And Synthesis
Synthesis
4-Chloropyridine-2-carboxylic acid

5470-22-4

N,O-Dimethylhydroxylamine hydrochloride

6638-79-5

4-chloro-N-methoxy-N-methylpicolinamide

757251-62-0

N,O-dimethylhydroxylamine hydrochloride (4.6 g, 47.61 mmol) was dissolved in DMF (50 mL) at 0 °C, followed by the addition of DIPEA (16.9 mL, 95.23 mmol) and the mixture was stirred for 10 min. Next, 4-chloropyridine-2-carboxylic acid (5.0 g, 31.74 mmol) and HATU (17.8 g, 47.61 mmol) were added and the reaction mixture was stirred for 16 hours at room temperature. After completion of the reaction, the solvent was removed by vacuum concentration and the product was purified by silica gel column chromatography using a hexane solution of 15-20% ethyl acetate as eluent to give 4-chloro-N-methoxy-N-methylpyridine-2-carboxamide (4.8 g, 96% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.37 (s, 3H), 3.72 (s, 3H), 7.35 (d, 1H), 7.63 (br s, 1H), 7.48 (d, 1H). the LCMS analysis showed a retention time of Rt = 2.30 min and a mass spectrum of m/z 201 [M + H]+ .

References[1] Patent: WO2014/53967, 2014, A1. Location in patent: Page/Page column 151
[2] Patent: WO2015/138208, 2015, A1. Location in patent: Page/Page column 10-11
4-chloro-N-methoxy-N-methylpicolinamide Preparation Products And Raw materials
Raw materials4-Chloropyridine-2-carboxylic acid-->N,O-Dimethylhydroxylamine hydrochloride-->N,N-Diisopropylethylamine-->N,N-Dimethylformamide
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