Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-amino-4-hydroxybenzoate

HRID 350367

Reaction equation

HRID 350367 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

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 10815Methyl 3-amino-4-hydroxybenzoateYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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

  1. customInsoluble catalyst was removed
  2. customthe filtrate was evaporated in vacuo
  3. 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

Linked notes

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