Toluene → 4-(2-Aminophenyl)butyronitrile

Participants

Reaction Steps

450 mg of 4-(2-nitrophenyl)butyronitrile, dissolved in 12.5 ml of methanol, are added dropwise to a mixture of 412 mg of iron powder (7.5 mmol) and 663 mg of ammonium chloride (12.5 mmol) in 12.5 ml of water at room temperature and under protective gas in a 100 ml glass round-bottomed flask. The mixture is heated for 5 hours with reflux. 25 ml of water are added to the cooled mixture and extraction is performed with toluene. The combined toluene phases are dried and the solvent distilled off under reduced pressure. The residue is purified by column chromatography on silica gel (eluent toluene/ethyl acetate 10:1 v/v). Yield: 276 mg (1.73 mmol, 72%).

Provenance & Evidence