Water → 2-Amino-3-fluorobenzoic acid

HRID 2082564Notes

Reaction equation

HRID 2082564 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10]CC[C:7]2=[O:12].C([O:17]O)(C)(C)C.C[O-].[Na+].O>CO.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:7]([OH:12])=[O:17])[C:11]=1[NH2:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxide2×HCID 10942334Sodium Methoxide2×HCID 197787528-Fluoro-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 5864082-Amino-3-fluorobenzoic acidYield 51.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×

Procedure

A solution of 0.25 g (1.5 mmol) of 8-fluoro-2,3-dihydroquinolin-4-one, 0.8 g (6.2 mmol) of 70 percent t-butyl hydroperoxide, 2 mL of 25 percent sodium methoxide in methanol and 3 mL of methanol were stirred at 75° C. for 72 hr. An additional 1 mL of 70 percent t-butyl hydroperoxide and 2 mL of 25 percent sodium methoxide in methanol were added and heating was continued for 72 more hr. The reaction mixture was cooled, poured into water and neutralized with acetic acid. The mixture was extracted with methylene chloride and the organic phase was collected. Evaporation of the solvent gave 0.12 g (51 percent yield) of 3-fluoroanthranilic acid, identical in all respects to an authentic sample.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with methylene chloride
  4. customthe organic phase was collected
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-df375400ab0d471ea7b5c632dc82443c
Source dataset
uspto-grants-1993_02
Patent number
US05189210

Reaction notes

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