Water → 2-Amino-3-fluorobenzoic acid

Participants

Reaction Steps

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.

Provenance & Evidence