Methanamine, N-methoxy-, hydrochloride (1:1) → 6-Chloro-N-methoxy-N-methylnicotinamide

To a solution of 6-chloronicotinoyl chloride (2 g, 11.4 mmol) and diethylisopropylamine (5 mL, 28.5 mmol) in dichloromethane (100 mL) was added N,O-dimethylhyroxylamine hydrochloride (1.22 g, 12.5 mmol) at 0° C. The solution was allowed to warm to room temperature then was stirred for 48 hours. The mixture was washed with 20% aqueous citric acid (2×100 mL), 1N aqueous sodium hydroxide (2×100 mL), brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford 6-chloro-N-methyl-N-(methyloxy)pyridine-3-carboxamide (2.05 g, 92% yield) as a yellow oil. 1H NMR (400 MHz, d6-DMSO): 8.65 (d, 1H), 8.08 (dd, 1H), 7.63 (d, 1H), 3.67 (s, 3H), 3.30 (s, 3H); MS (EI) for C8H9ClN2O2: 201 (MH+).

1. washThe mixture was washed with 20% aqueous citric acid (2×100 mL), 1N aqueous sodium hydroxide (2×100 mL), brine (100 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated

ORD record

ord-1f01014d6032419a95e3d9652230f308

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012956B2