Acetic Acid → (2,3-Diamino-5-chlorophenyl)methanol

Participants

Reaction Steps

(2-Amino-5-chloro-3-nitro-phenyl)-methanol (0.202 g, 1 mmol) was suspended in a mixture of iso-propanol (5 ml), water (2 ml), methanol (3 ml) and acetic acid (0.05 ml). Raney Nickel (0.015 g, as a slurry in water) was added carefully under nitrogen. The reaction mixture was shaken under a hydrogen atmosphere for 4 h, then diluted with methanol-water (1:1, 50 ml) and filtered to removed catalyst residues. Volatiles were removed in vacuo, and the remaining aqueous layer extracted with ethyl acetate (4×30 ml). The combined organics were washed with brine, dried (MgSO4) and reduced in vacuo to give (2,3-diamino-5-chloro-phenyl)-methanol as an orange solid (0.144 g, 84%). (LC/MS: Rt 0.85, [M+H]+ 173.03).

Provenance & Evidence