5-Bromo-N-tert-butyl-2-nitroaniline → 5-Bromo-1-N-tert-butylbenzene-1,2-diamine

Participants

Reaction Steps

A suspension of (5-bromo-2-nitro-phenyl)-tert-butyl-amine (Step 24.3) (6 g, 21.97 mmol) and Raney nickel (2 g) in MeOH/THF (1:1 v/v, 600 mL) is stirred for 9 h at rt, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. The residue purified by silica gel column chromatography (Hex/EtOAc, 97:3→3:1) to afford 4.4 g of the title compound as a black oil: ESI-MS: 243.0/245.0 [M+H]+; tR=2.75 min (System 1); TLC: Rf=0.89 (Hex/EtOAc, 1:1).

Provenance & Evidence