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

HRID 1845095Notes

Reaction equation

HRID 1845095 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]>[Pd].CO>[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-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.01 g (10 mmol) 2-hydroxy-3-nitro-benzoic acid methyl ester, 0.8 g of palladium (10 wt. % on carbon powder) and 30 mL of methanol was hydrogenated at 40 psi overnight. The reaction mixture was filtered over celite. Evaporation of the solvents in vacuo gave 3-Amino-2-hydroxy-benzoic acid methyl ester. LCMS: 168 (M+1)+.

Workup

  1. customwas hydrogenated at 40 psi overnight
  2. filtrationThe reaction mixture was filtered over celite
  3. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-67d2a7102a724cd5bd51a4eadbb21a1e
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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