Methylamine → 4-Chloro-N-methylpicolinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-pyridine-2-carbonyl chloride (27.6 g, 0.16 mol) in anhydrous THF (100 mL) at 0° C. was added dropwise a solution of MeNH2 in EtOH. The resulting mixture was stirred at 3° C. for 4 h. The reaction mixture was concentrated under reduced pressure to yield a solid, which was suspended in EtOAc and filtered. The filtrate was washed with brine (2×100 mL), dried and concentrated to yield 4-chloro-N-methylpicolinamide as a yellow solid (16.4 g, 60% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.78 (d, J=7.2 Hz, 1H), 8.54 (d, J=7.2 Hz, 1H), 7.95 (s, 1H), 7.67-7.65 (m, 1H), 2.79 (d, J=4.8 Hz, 3H); MS (ESI) m/z: 171 (M+H+).

Provenance & Evidence