Water → N-[5-(4-aminophenoxy)-2-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(1-cyano-1-methylethyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide (3.50 g, 8.0 mmol), calcium chloride (2.36 g, 21.2 mmol) and reduced iron (4.75 g, 85 mmol) in ethanol (180 mL)/water (20 mL) was stirred with heating at 80° C. for 10 hr. The reaction mixture was cooled to room temperature, passed through a pad filled with celite to separate insoluble material, and the insoluble material was washed with ethanol. The filtrate and the washing were combined and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with 5% aqueous ammonium chloride solution (200 mL), water (200 mL), 5% aqueous sodium hydrogencarbonate solution (200 mL) and saturated brine (200 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40→0/100), and the obtained solution was concentrated under reduced pressure to give the title compound (2.89 g, 94%) as a colorless amorphous substance.

Provenance & Evidence