1,2-Dichloroethane → 2-Chloro-N-methoxy-N-methylisonicotinamide

Participants

Reaction Steps

2-Chloroisonicotinic acid (12-2, 2.0 g, 12.7 mmole), N,O-dimethylhydroxylamine hydrochloride (3.71 g, 38.1 mmole), EDC (2.92 g, 15.2 mmole), and HOBt (2.06 g, 15.2 mmole) were combined in dry DMF (40 mL). To this was added Et3N (8.9 mL, 63.47 mmole) at RT. After 60 hr the mixture was diluted with H2O and extracted with EtOAc (4×). The combined organic layers were washed with H2O, brine; then dried (MgSO4), filtered, and concentrated to give the titled compound as an amber oil which solidified on standing. The material was sufficiently pure for use in the next step. 1H-NMR (500 MHz, CDCl3) δ8.47 (d, 1H, J=5.13 Hz), 7.57 (s, 1H), 7.45 (m, 1H), 3.56 (s, 3H), 3.38 (s, 3H).

Provenance & Evidence