Water → N-[3-(4-aminophenoxy)-4-methoxyphenyl]-3-(1-cyanocyclopropyl)benzamide

Participants

Reaction Steps

A solution of 3-(1-cyanocyclopropyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide (2.10 g, 4.89 mmol), reduced iron (0.56 g, 10.0 mmol) and calcium chloride (1.11 g, 10.0 mmol) in ethanol (40 mL)/water (10 mL) was stirred at 80° C. for 18 hr. The reaction mixture was poured into 0.5N aqueous sodium hydroxide solution (400 mL), ethyl acetate (300 mL) was added and the mixture was stirred. The insoluble material was filtered off through celite, and the organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (1.74 g, 82%) as a pale-yellow solid.

Provenance & Evidence