2,6-Difluoro-4-nitrobenzoic acid → 4-Amino-2,6-difluorobenzoic acid

HRID 634685Notes

Reaction equation

HRID 634685 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].[H][H]>[Pd].C(O)C>[NH2:11][C:9]1[CH:8]=[C:7]([F:14])[C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1

Participants

5

Reactant 2

HCID 212603012,6-Difluoro-4-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 109759644-Amino-2,6-difluorobenzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,6-difluoro-4-nitrobenzoic acid (2.5 g, 12 mmol) and 10% palladium-on-charcoal catalyst (500 mg) in ethanol (I50 ml) was stirred under 1 atmosphere of hydrogen at ambient temperature for 3 hours. The catalyst was removed by filtration through diatomaceous earth, the filter pad washed with ethanol and the solvent removed by evaporation to give 4-amino-2,6-difluorobenzoic acid (3-8 g, 91%).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad washed with ethanol
  3. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-e4a795f2c67d4d1583d69289e92806c9
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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