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

HRID 354305Notes

Reaction equation

HRID 354305 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 (30 mL) 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-70ec77a158a84a04b954393d2b13a7d2
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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