Hydrazine hydrate (1:1) → 4-Nitrobenzylamine

Participants

Reaction Steps

2-(4-Nitrobenzyl)isoindoline-1,3-dione (1.6 g, 5.67 mmol) was dissolved in tetrahydrofuran (8 mL). To the solution hydrazine monohydrate (1.7 mL, 22.675 mmol) and p-toluenesulfonic acid monohydrate (108 mg, 0.57 mmol) was added. It was refluxed for 6 h. TLC showed complete consumption of starting material. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give (4-nitrophenyl)methanamine (715 mg, 83%).

Provenance & Evidence