Hydrazine hydrate (1:1) → 4-Nitrobenzylamine

Participants

Reaction Steps

To a solution of 2-(4-nitrobenzyl)isoindoline-1,3-dione (1.6 g, 5.33 mmol) in tetrahydrofuran was added hydrazine monohydrate (4 eq). The mixture was refluxed for 6 h. After cooling down to room temperature the mixture was treated with potassium bicarbonate to pH 12˜13, extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave (4-nitrophenyl)methanamine (592 mg, 65%).

Provenance & Evidence