Borane → 2-(Aminomethyl)-4-nitroaniline hydrochloride

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Reaction Steps

Borane in THF (400 ml, 0.40 mol) is added dropwise to 2-amino-5-nitrobenzonitrile (60 g, 0.35 mol) in THF (600 ml) at 0° C. The mixture is allowed to warm to room temperature and is stirred for 16 hours. The resulting mixture is cooled to 0° C. and 200 ml of absolute ethanol/HCl are added. The THF is removed and the product is filtered off and recrystallized from isopropyl ether. Yield: 68.8 g (96%); Rf (1:1 methanol/chloroform): 0.15; IR (KBr): 3416, 2980, 1669, 1601, 1474, 1285 cm−1.

Provenance & Evidence