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

HRID 1990878Notes

Reaction equation

HRID 1990878 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].[H][H]>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

5

Reactant 2

HCID 596904Methyl 2-hydroxy-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoateYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-hydroxy-3-nitro-benzoic acid methyl ester (2.3 g, 11.67 mmol, 1.0 equiv) in ethanol (50 mL) was added palladium on activated charcoal 10% (0.47 g, 0.47 mmol, 0.04 equiv), the reaction vessel filled with hydrogen (3.5 bar) and stirred at 80° C. for 2 h. The catalyst was removed by filtration over celite and the solvent removed under reduced pressure yielding 1.9 g (95%) of the title compound which was used directly without further purification. 1H NMR (300 MHz, CDCl3): δ 3.88 (br s, 2H), 3.93 (s, 3H), 6.71 (t, J=7.9 Hz, 1H), 6.87 (dd, J=7.9 Hz, J=1.5 Hz, 1H), 7.24 (dd, J=7.9 Hz, J=1.5 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 52.13, 111.83, 118.71, 118.98, 119.55, 135.85, 149.70, 171.11.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b4777477cb534dfe8f92aac06ab10dbf
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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