Methanamine, N-methoxy-, hydrochloride (1:1) → 5-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamide

Participants

Reaction Steps

To a solution of acid chloride 59 (3.41 g, 14.3 mmol) in CH2Cl2 (70 mL) was added dropwise N,O-dimethylhydroxylamine hydrochloride (4.18 g, 42.9 mmol) at 0° C. under an atmosphere of nitrogen. Then, TEA (12.0 mL, 85.8 mmol) was added to the mixture at 0° C. After being stirred for 18 hours, the mixture was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 60 (3.45 g, 80%) as a white solid.

Provenance & Evidence