Ammonium Chloride → (+/-)-3-(3-Aminophenyl)-5-(2,6-dichlorophenyl)-2-isoxazoline

Iron powder (99 mg, 1.78 mmol) was added into a suspension of (±)-5-(2,6-dichlorophenyl)-3-(3-nitrophenyl)-2-isoxazoline (100 mg, 0.297 mmol) in ethanol/water (2/1) under nitrogen. The mixture was stirred for 10 min, followed by the addition of ammonium chloride (32 mg, 0.594 mmol). The reaction was stirred for 20 min at room temperature, followed by heating at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and filtered through a plug of Celite. The filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with aqueous sodium bicarbonate solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with 8:2 hexanes-ethyl acetate to provide the title compound as a light yellow solid.