Ammonium Hydroxide → 4-Chloropyridine-2-carboxamide

Participants

Reaction Steps

4-Chloro-pyridine-2-carboxylic acid methyl ester (2) (500 mg, 3 mmol) was dissolved in MeOH (5 ml) and concentrated ammonium hydroxide (5 ml) was added. After 10 minutes, the reaction mixture was partitioned between ethyl acetate and brine. The ethyl acetate was washed with brine one additional time, and the solvents were removed under vacuum to yield the title product 3 (400 mg (85%), 2.5 mmol) as a white solid. 1H NMR (DMSO-d6): δ 8.64 (d, J=5.3 Hz, 1H), 8.22 (bs, 1H), 8.03 (d, J=1.9 Hz, 1H), 7.83 (bs, 1H), 7.68 (dd, J=5.3 Hz, 1.9 Hz, 1H). MS (ESI-POS): [M+H]+=157.

Provenance & Evidence