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

(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).

1. filtrationfiltered
2. customto removed catalyst residues
3. customVolatiles were removed in vacuo
4. extractionthe remaining aqueous layer extracted with ethyl acetate (4×30 ml)
5. washThe combined organics were washed with brine
6. dry with materialdried (MgSO4)

ORD record

ord-706720417bb0454dacceaae038451cfc

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977477B2