Water → 5-amino-1H-isochromen-1-one

Participants

Reaction Steps

Tin(II)chloride dihydrate (41.9 g, 185.7 mmol) was added to a stirred solution of 5-nitro-1H-isochromen-1-one (7.1 g, 37.1 mmol) in anhydrous tetrahydrofuran (120 mL). The reaction mixture was stirred at room temperature for 18 h. The resulting mixture was diluted with ethyl acetate (400 mL) and treated with saturated aqueous sodium bicarbonate to pH=10. Water (100 mL) was added and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×150 mL) and the combined organic fractions were dried over sodium sulfate, filtered and evaporated to yield 5-amino-1H-isochromen-1-one (5.8 g, 36.0 mmol, 97%) as a yellow solid.

Provenance & Evidence