Sodium Hydroxide → 2-Amino-4,5-difluorobenzoic acid

HRID 982200Notes

Reaction equation

HRID 982200 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.[OH-].[Na+].C([O-])=O.[Na+]>[Pd].O>[F:13][C:11]1[CH:12]=[C:4]([NH2:1])[C:5](=[CH:9][C:10]=1[F:14])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723810Sodium FormateHCID 42196304,5-Difluoro-2-nitrobenzoic acid

Product 1

HCID 7359652-Amino-4,5-difluorobenzoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-nitro-4,5-difluorobenzoic acid (1.0 g) was added to 10 mL of water. 0.2 g of NaOH was added, followed by 1.0 g of sodium formate. 0.05 g of 10% palladium on carbon was added, and the mixture was heated to 90° C. for 2.5 h. After cooling, a suitable internal standard was added. 19F NMR internal standard analysis of the entire reaction mixture indicated a 93% yield of 4,5-difluoroanthranilic acid.

Workup

  1. temperatureAfter cooling
  2. additiona suitable internal standard was added
  3. custom19F NMR internal standard analysis of the entire reaction mixture

Sources & evidence

ORD record
ord-6fcea16c66834bd38bddcf85ae77586f
Source dataset
uspto-grants-1991_02
Patent number
US04994606

Reaction notes

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