Water → 2-Amino-3-fluorobenzoic acid

HRID 2082563Notes

Reaction equation

HRID 2082563 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10]C(=O)C[C:7]2=[O:13].C([O:18]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:13])=[O:18])[C:11]=1[NH2:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxide2×HCID 10942334Sodium Methoxide2×HCID 117452058-Fluoroquinoline-2,4(1H,3H)-dione

Product 1

HCID 5864082-Amino-3-fluorobenzoic acidYield 376%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×

Procedure

A solution of 0.1 g (0.6 mmol) of 8-fluoroquinolin-2,4-dione, 0.1 g (7.8 mmol) of 70 percent t-butyl hydroperoxide, 0.2 g of 25 percent sodium methoxide in methanol and an additional 2 mL of methanol was heated at 75° C. with stirring for 48 hr. An additional 0.2 g of t-butyl hydroperoxide and 0.5 mL of 25 percent sodium methoxide in methanol were added and heating was continued for 24 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 0.35 g (40 percent yield) of 3-fluoroanthranilic acid, mp 172° C.

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-4e02aa1da6bf40b8bf6f975e23724a31
Source dataset
uspto-grants-1993_02
Patent number
US05189210

Reaction notes

Loading…