2,4-Difluoro-5-nitrobenzoic acid → 5-Amino-2,4-difluorobenzoic acid

HRID 6864Notes

Reaction equation

HRID 6864 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>C(O)C.[Pd]>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([NH2:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 27828222,4-Difluoro-5-nitrobenzoic acid

Product 1

HCID 210494315-Amino-2,4-difluorobenzoic acidYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,4-difluoro-5-nitrobenzoic acid (0.998 g, 4.91 mmol) in ethanol (50 mL) was added 10% palladium on charcoal (107 mg) and the mixture was hydrogenated at 30 psi. After 2 h, the mixture was degassed, filtered and the filtrate was concentrated in vacuo to afford 2,4-difluoro-5-aminobenzoic acid (0.83 g, 97%) as tan solid. LC/MS (ESI); (M-H)−=172.

Workup

  1. customthe mixture was degassed
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0f6298eabc42429f85799e265714a6cf
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Reaction notes

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