Hydrochloric Acid → 4-(3-Amino-phenoxy)-N-(3-bromo-phenyl)-3-nitro-benzamide

Participants

Reaction Steps

A solution of N-(3-Bromo-phenyl)-4-chloro-3-nitro-benzamide (from Example 16A) (0.71 g, 2.0 mmol), 3-aminophenol (0.22 g, 2.0 mmol) and powdered potassium hydroxide (0.23 g, 4.0 mmol) in Dimethyl sulfoxide (5 mL) was heated at 100° C. for 30 minutes. After cooling to room temperature the mixture was poured into ice water (100 mL) and the resultant solution adjusted to pH 5 with 1N aqueous hydrochloric acid. The solution was then extracted with ethyl acetate (3×50 mL), the combined extracts dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound (0.8 g, 93%).

Provenance & Evidence