Hydrochloric Acid → 2-Amino-4,6-difluorobenzoic acid

HRID 1826259Notes

Reaction equation

HRID 1826259 reaction equation
[OH:1]O.[F:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[C:6](=[O:15])C(=O)[NH:8]2.[OH-].[Na+].Cl>>[NH2:8][C:9]1[CH:10]=[C:11]([F:13])[CH:12]=[C:4]([F:3])[C:5]=1[C:6]([OH:15])=[O:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 146519894,6-Difluoro-1H-indole-2,3-dione

Product 1

HCID 146519722-Amino-4,6-difluorobenzoic acid

Conditions

Temperature
70 °C

Procedure

Hydrogen peroxide (35% solution in water, 23 ml) was added dropwise to a stirred solution of 4,6-difluoro-2,3-dioxoindoline (14 g) in a concentrated aqueous sodium hydroxide solution (33%, 115 ml) that was heated to 70° C. The mixture was heated to 70° C. for 15 minutes. The resultant mixture was cooled to 0° C. and the the mixture was acidified to pH4 by the addition of concentrated aqueous hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulphate and evaporated to give 2-amino-4,6-difluorobenzoic acid (12 g); NMR Spectrum: (DMSOd6) 6.25 (m, 1H), 6.38 (m, 1H).

Workup

  1. temperatureThe mixture was heated to 70° C. for 15 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-8b91bc3e54e2496b9635a3069d36a962
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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