Hydrazine hydrate (1:1) → (2-Fluoro-4-nitrophenyl)methanamine

Participants

Reaction Steps

To a stirred solution of 2-(2-fluoro-4-nitrobenzyl)isoindoline-1,3-dione (500 mg, 1.665 mmol) in tetrahydrofuran were added hydrazine monohydrate (333 mg, 6.661 mmol) and p-toluenesulfonic acid monohydrate (29 mg, 0.167 mmol). The reaction mixture was refluxed for 6 h, then cooled to room temperature, diluted with ethyl acetate. The mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography to give (2-fluoro-4-nitrophenyl)methanamine (194 mg, 68%).

Provenance & Evidence