Ammonium Chloride → N-(4-chlorophenyl)benzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of EtOH (100 ml) and NH4Cl saturated solution (15 ml), N-(4-chlorophenyl)-2-nitrobenzenamine (5.0 g, 20.1 mmol) was added, followed by iron powder (4.0 g). The reaction mixture was heated at 70° C. for 2 h. The solid was filtered and the filtrate was extracted by EA (100 mL×3), dried over Na2SO4. After the solvent was removed, the mixture was purified by Combi-flash (PE:EA=5:1) to give N1-(4-chlorophenyl)benzene-1,2-diamine (4.1 g, 93.2%) as a light yellow solid. LRMS (M+H+) m/z: calcd 218.06. found 218. 1H NMR (300 MHz, CD3OD): δ 6.52-6.59 (m, 3H), 6.70-6.74 (m, 1H), 6.81-6.87 (m, 1H), 6.90-6.99 (m, 3H).

Provenance & Evidence