[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=2)[CH2:13][C:12]1=[O:21].C([OH:24])C>O>[CH3:20][C:16]1[CH:17]=[CH:18][C:19]([NH:11][C:3]2[C:4]([F:10])=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=2[F:1])=[C:14]([CH2:13][C:12]([OH:21])=[O:24])[CH:15]=1The suspension of 350 mg of N-(2′,3′,4′,6′-tetrafluorophenyl)-5-methyloxindole in 20 ml of ethanol and 5 ml of water is degassed by passing through nitrogen for 1.5 h. Then 260 mg of 30% aqueous sodium hydroxide is added and the mixture is heated to reflux for 6.5 hours. Most of the ethanol is then removed by distillation the mixture is cooled to room temperature followed by the slow addition of 1N hydrochloric acid (1.05 g) to reach a pH of about 3. The precipitate is then filtered, washed with ethanol/water (1:1) and dried in vacuo at room temperature affording the title product.
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