Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methylbenzamide

Participants

Reaction Steps

TBTU (4.73 g, 14.7 mmol) was added to a solution of 3-{(4-chloro-2-methoxybenzoyl)amino}benzoic acid (4.50 g, 14.7 mmol), N,O-dimethylhydroxylamine hydrochloride (1.72 g, 17.7 mmol) and i-Pr2NEt (7.60 g, 58.9 mmol) in DMF (29 mL) at 25°. The reaction mixture was stirred at 25° for 2.5 h. The mixture was diluted with EtOAc (200 mL). The resulting solution was successively washed with aqueous 1 N HCl (2×75 mL), water (2×75 mL), aqueous saturated NaHCO3 (2×75 mL) and brine (75 mL), then dried (MgSO4), filtered and concentrated under reduced pressure to give the corresponding N-methoxy-N-methylbenzamide of formula 6 (4.32 g, 84% yield) as a white solid:

Provenance & Evidence