Hydrazine → 4-(diethylaminomethyl)aniline

Participants

Reaction Steps

To a suspension of N-ethyl-N-(4-nitrobenzyl)ethanamine (335 mg, 1.61 mmol) and Raney Ni (50 mg) in refluxing ethanol (10 mL) was added drop-wise anhydrous hydrazine (0.5 mL). After the addition was complete, the mixture was refluxed for an additional 20 minutes and then filtered through a pad of Celite. The Celite bed was washed with ethanol (100 mL) and the combined solution was evaporated under reduced pressure to provide pure 4-((diethylamino)methyl)aniline (262 mg, 91%).

Provenance & Evidence