Methyl 4-[2-(2-benzyloxyphenyl)ethenyl)-3-nitrobenzoate → 4-[2-Benzyloxyphenethyl]-3-aminobenzoic acid

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[CH:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][C:18]=1[N+:27]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Rh]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1[NH2:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A mixture of methyl 4-[2-(2-benzyloxyphenyl)ethenyl)-3-nitrobenzoate (2.5 g) and 5% Rhodium on alumina (520 mg) in ethanol (200 ml) was stirred under 1 atm. of hydrogen for 20 hours. The mixture was filtered and the solvent evaporated. The residue was purified by subjecting to chromatography using ethylacetate: dichloromethane (9:1) as eluant. There was thus obtained methyl 4-[2-(2-benzyloxyphenyl)ethyl]-3-aminobenzoate (1.71 g).