N-(2-Amino-4-chlorophenyl)anthranilic acid → 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

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A solution of 2-[(2-amino-4-chlorophenyl)amino]benzoic acid (11.8 g, 45 mmol) in xylene (150 mL) was heated to reflux in a Dean-Stark apparatus. The reaction mixture was stirred at reflux temperature for 31 h. After removal of the xylene in vacuo, the title compound was obtained. There was still starting material present. Therefore the product was dissolved in xylene (150 mL) again and stirring was continued overnight at reflux temperature in a Dean-Stark apparatus. After removal of the xylene under reduced pressure the title compound (12.4 g, 50.6 mmol) was obtained.

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