Acetic Acid → 4-Amino-2-fluorobenzoic acid

HRID 57226

Reaction equation

HRID 57226 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-2272ef503ec54d5b831c7c1d91da81fd
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Linked notes

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