Dimethylformamide → 4-fluoro-2-(2-fluoro-phenylamino)-N-methoxy-N-methyl-benzamide

Participants

Reaction Steps

In a 500 mL round bottom flask, 4-fluoro-2-(2-fluoro-phenylamino)-benzoic acid (6.0 g, 24.1 mmol), O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluorophosphate (HBTU) (18.5 g, 48 mmol) and triethylamine (20 mL, 144 mmol) were added to DMF (80.0 mL). The reaction mixture was stirred for 1 hr. at room temperature, then N,O-dimethylhydroxylamine hydrochloride (4.7 g, 48 mmol) was added. The mixture was stirred for 2 hr. The reaction mixture was poured into 300 mL of ethyl acetate and washed with saturated ammonium chloride (2×150 mL), water (2×200 mL) and brine (1×200 mL). The organic layer was evaporated and purified by flash chromatography using 30% ethyl acetate-hexanes to give 4-fluoro-2-(2-fluoro-phenylamino)-N-methoxy-N-methyl-benzamide (6.0 g, 85.3%).

Provenance & Evidence