2-Methoxy-6-nitrobenzoic acid → 2-Amino-6-methoxybenzoic Acid

HRID 3112Notes

Reaction equation

HRID 3112 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]([N+:12]([O-])=O)[CH:6]=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:12][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 133000352-Methoxy-6-nitrobenzoic acid

Product 1

HCID 27353572-Amino-6-methoxybenzoic AcidYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-methoxy-2-nitrobenzoic acid (3.25 g, 16.5 mM) in ethanol (180 mL) containing 10% palladium-on-carbon catalyst (0.30g) was hydrogenated using a Parr apparatus. When hydrogen consumption ceased, the resulting mixture was filtered through diatomaceous earth and the filtrate concentrated to provide the title benzoic acid (2.76 g, 100%) as a tan solid; MS(CI): 168 (M+H).

Workup

  1. customWhen hydrogen consumption
  2. filtrationthe resulting mixture was filtered through diatomaceous earth
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-49d860bfec704ababf3ed788e3799c62
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Reaction notes

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