[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]
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.
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