Methyl 2-hydroxy-3-nitrobenzoate → Methyl 3-amino-2-hydroxybenzoate

HRID 2114513Notes

Reaction equation

HRID 2114513 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[OH:13]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[OH:13]

Participants

4

Reactant 1

HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoateYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-hydroxy-3-nitrobenzoic acid methyl ester (5 g, 25.4 mmol) in ethanol (40 mL) was added 10% palladium on carbon (0.5 g), and the mixture was hydrogenated for 2 h. The catalyst was removed via filtration and the solvent was removed via evaporation, yielding 4.17 g (88%) of title compound 3-amino-2-hydroxybenzoic acid methyl ester, 1l.

Workup

  1. customThe catalyst was removed via filtration
  2. customthe solvent was removed via evaporation

Sources & evidence

ORD record
ord-34cfc5f20109492c94c76def55d161ba
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

Loading…