Methanamine, N-methoxy-, hydrochloride (1:1) → 2-Chloro-N-methoxy-N-methylnicotinamide

Participants

Reaction Steps

2-Chloronicotinoyl chloride (36 g, 0.20 mol) was dissolved in tetrahydrofuran (290 mL) and separately N,O-dimethylhydroxylamine hydrochloride (48 g, 0.49 mol) was stirred in 290 mL saturated bicarbonate solution until the degassing subsided. Then the bicarbonate solution was added to the acid chloride solution and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate (2×), dried over sodium sulfate, filtered and evaporated to give the desired product (34 g, 83%). LCMS for C8H10ClN2O2 (M+H)+: m/z=201.0. Found: 200.9.

Provenance & Evidence