Hydrochloric Acid → 2-Amino-3-fluorobenzoic acid

HRID 497988

Reaction equation

HRID 497988 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9]C(=O)[C:7]2=[O:12].[OH:13]O.Cl>[OH-].[Na+]>[NH2:9][C:10]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:12])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 5864187-Fluoroisatin

Product 1

HCID 5864082-Amino-3-fluorobenzoic acidYield 59%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 7-fluoro-1H-indol-2,3-dione (13.0 g, 78.7 mmol) in 10N sodium hydroxide (125 mL) was heated and stirred at 70° C. for 1 hour. 30% Hydrogen peroxide (25 mL) was added dropwise over 20 minutes at the same temperature, and the mixture was heated and stirred at the same temperature further for 1 hour. The solution was ice cooled, and conc. hydrochloric acid was added to the solution carefully until the pH of the solution became 4. Organic matter was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The crystals thus obtained were collected by filtration to give the title compound (7.15 g, 59% yield).

Workup

  1. temperaturethe mixture was heated
  2. stirringstirred at the same temperature further for 1 hour
  3. temperaturecooled
  4. extractionOrganic matter was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crystals thus obtained
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3705cbb6689f434d9c94762859f11cd1
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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