Acetic Acid → (2-Amino-3-chlorophenyl)amine

Participants

Reaction Steps

3-Chloro-2-nitro-aniline (0.345 g, 2 mmol) was dissolved in iso-propanol (10 ml) and water (2 ml). Catalytic acetic acid (0.1 ml) was added, followed by Raney nickel (0.02 g, as 50% slurry in H2O) under a flow of nitrogen. The reaction mixture was then shaken under an atmosphere of hydrogen at ambient temperature for 5 hours and the catalyst was removed by filtration under a nitrogen atmosphere. The filtrate was reduced in vacuo, partitioned between ethyl acetate and water, and the organic layer reduced in vacuo to give 3-chloro-benzene-1,2-diamine as a brown oil (0.190 g, 67%). (LC/MS: Rt 1.84, [M+H]+ 143.07).

Provenance & Evidence