Acetic Acid → 4-Amino-2-fluorobenzoic acid

HRID 2261625Notes

Reaction equation

HRID 2261625 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)(=O)C>[Pd].CO>[NH2:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 3026804-Amino-2-fluorobenzoic acidYield 102.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitrobenzoic acid (1.0 g, 5.4 mmol) in 20 mL of a mixture of acetic acid and methanol (1:1), was added a catalytic amount of palladium on charcoal (25 mg). The reaction was stirred under an atmosphere of hydrogen gas at room temperature overnight. The mixture was then filtered through celite and the solvent was removed by evaporation to yield 0.86 g (100%) of the title compound as a cream coloured solid.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-e54b59d1e91c40ee878e3f9c3e09b078
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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