N-{2-chloro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide → N-{5-[(5-aminopyridin-2-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

Participants

Reaction Conditions

Reaction Steps

N-{2-Chloro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (13 g, 35.9 mmol) was dissolved in acetic acid (200 mL), reduced iron (10 g, 179 mmol) was added, and the mixture was stirred at 60° C. for 3 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The concentrated solution was diluted with ethyl acetate (150 mL), aqueous sodium hydrogen carbonate solution (200 mL) was slowly added, and the mixture was filtered through celite. The organic layer was collected, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residual oil was dissolved in toluene, and the solution was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→20/80) to give the title compound (10.9 g, 91%) as a brown oil.

Provenance & Evidence