Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

HRID 1773493Notes

Reaction equation

HRID 1773493 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH3:14])[CH:5]=1>[Pd].CO.ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

5

Reactant 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 602411Methyl 4-amino-3-methoxybenzoateYield 100.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, catalytic amount) was added to a solution of 3-methoxy-4-nitro-benzoic acid methyl ester (1.08 g, 5.11 mmol) in a mixture of methanol (40 mL) and dichloromethane (a few drops). The resulting mixture was stirred under nitrogen atmosphere (balloon pressure) overnight. The catalyst was filtered off on a CELITE™ pad and the solvent was evaporated to give 0.929 g of 4-amino-3-methoxy-benzoic acid methyl ester as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered off on a CELITE™ pad
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-242fabdb9c2641d4a0f448955064f473
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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