[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]#N)[C:10]1=[O:18].BrC1C=C(F)C=CC=1N1C=CC(C)=C(C#N)C1=[O:36].S(=O)(=O)(O)O.[OH-:42].[Na+]>O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([OH:36])=[O:42])[C:10]1=[O:18]To a mixture of 1-(2-bromo-4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 1-(2-bromo-4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (2.00 g, 6.51 mmol) and water (10 mL) was added conc. sulfuric acid (10 mL) at 0° C., and the mixture was stirred at 100° C. for 16 hr. After cooling to 0° C., the mixture was basified (pH 11) with 8N aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified (pH 4) with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (1.12 g, 53%) as a white powder.
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