C1(C)C(S([C:10]2[CH:11]=[C:12]([NH2:19])[C:13](=[CH:17][CH:18]=2)[C:14]([OH:16])=O)(=O)=O)=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[NH2:19][C:12]1[CH:11]=[CH:10][CH:18]=[CH:17][C:13]=1[C:14]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:17][CH:18]=1)=[O:16]The mixture of 14.6 g (0.050 mol) of p-toluenesulfonylanthranilic acid prepared in Example 8 and 11.9 g (0.057 mol) of phosphorus pentachloride in 150 ml of dry benzene were heated at about 50° C. for 0.5 h. Cooled to 20-25° C. and 29.0 g (0.218 mol) of anhydrous aluminum chloride was added in portions. When addition was complete, the mixture was heated at 80-90° C. for 4 h and then cooled, poured onto a mixture of ice and 60 ml of 1N hydrochloride acid. The benzene was removed by vacuo distillation, the crude product was separated by filtration and washed with sodium carbonate and water. The filter cake is sucked reasonably dry, dissolved in 160 ml of conc. sulfuric acid and heated to 120° C. for 15 minutes. The reaction mixture was cooled and poured onto the mixture of ice and 1 g of norit, and the solution is filtered. The filtrate was neutralized with 12N ammonium hydroxide. The solid filtered off, washed with water and dried, recrystallized from 95% ethanol to give the title compound (6.63 g) as yellow crystal, yield 65.0%, m.p. 105-106° C.
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