Ammonium Chloride → Ethyl 6-aminobenzo[d]isoxazole-3-carboxylate

Participants

Reaction Steps

Ethyl 6-nitrobenzo[d]isoxazole-3-carboxylate (12.7 mmol), iron (53.6 mmol), and ammonium chloride (56.1 mmol) were combined and diluted with ethanol (150 mL) and water (20 mL). The resulting suspension was heated at reflux, with vigorous stirring, for 2 h. The reaction mixture was filtered through Celite, diluted with brine (200 mL), and the resulting solution was extracted with ethyl acetate (200 mL). The organic layer was washed with of brine (3×200 mL), dried (magnesium sulfate), and concentrated. The residue was purified by chromatography (20/1 petroleum ether/ethyl acetate) to provide ethyl 6-aminobenzo[d]isoxazole-3-carboxylate 49.6% yield as a orange solid

Provenance & Evidence