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

HRID 1360228Notes

Reaction equation

HRID 1360228 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([NH2:11])[CH:5]=1

Participants

4

Reactant 1

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

Product 1

HCID 10815Methyl 3-amino-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-hydroxy-3-nitro-benzoic acid methyl ester (5.0 g, 25.4 mmol) in ethanol (120 mL) was treated with 5% palladium on active carbon (0.24 g, 2.3 mmol, 0.1 equiv.) and the flask was evacuated and placed under an hydrogen atmosphere. The mixture was stirred vigorously for 2 h and 45′, the palladium was filtered off, washing extensively with ethanol. The solvent was removed in vacuo to yield 3-amino-4-hydroxy-benzoic acid methyl ester as a white solid, 4.2 g (100%), MS (ISP): m/e=168.3 (M+H+). This was used crude in the following reaction.

Workup

  1. customthe flask was evacuated
  2. filtration45′, the palladium was filtered off
  3. washwashing extensively with ethanol
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b41a7d29b5124fd49b0ccab86387f5d1
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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