Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-amino-4-hydroxybenzoate
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred mixture of methyl 4-hydroxy-3-nitrobenzoate (3.22 g, 0.0163 mol) and 5% Pd—C (12.9 g) in MeOH (30mL) was hydrogenated under an atmospheric pressure for 70 hr at room temp. Insoluble catalyst was removed, and the filtrate was evaporated in vacuo. The residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent to afford 1.89 g (69%) methyl 3-amino-4-hydroxybenzoate as a pale brown syrup.
Workup
- customInsoluble catalyst was removed
- customthe filtrate was evaporated in vacuo
- customThe residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent
Sources & evidence
- ORD record
- ord-795f063488d54799ad89dd33cb14ff31
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179819B2
Reaction notes
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