Water → N-{5-[(5-aminopyridin-2-yl)oxy]-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-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (2.5 g, 6.0 mmol), calcium chloride (1.75 g, 15 mmol) and reduced iron (4.03 g, 72 mmol) in ethanol (300 mL)/water (30 mL) was stirred with heating at 80° C. for 2 days. After the reaction mixture was cooled to room temperature, the insoluble material was filtered off through a pad filled with celite, and washed with ethanol. The filtrate and washing solution were combined, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogen carbonate solution (300 mL×2), water (300 mL) and saturated brine (300 mL), 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=50/50→0/100), and the obtained solution was concentrated under reduced pressure to give the title compound (2.31 g, 99%) as a pale-yellow amorphous substance.

Provenance & Evidence