Reaction of anthranilic acid and methoxy- and nitro-substituted anthranilic acid with p-toluenesulfonyl chloride in pyridine
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The reaction of anthranilic acid and methoxy- and nitro-substituted anthranilic acid with p-toluenesulfonyl chloride in pyridine was investigated. Anthranilic acid and its methoxy-substituted derivatives react to give the corresponding 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-ones and N,N'-ditosyldianthranilides. At 20°C, 4-nitroanthranilic acid gives primarily 2-(2-amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one, while its tosyl derivative is obtained at 114°. The products of the reaction of 5-nitroanthranilic acid with p-toluenesulfonyl chloride are 2-nitro-11H-pyrido[2,1-b]quinazolin-11-one and 2-(2-amino-5-nitrophenyl)-6-nitro-4H-3, 1-benzoxazin-4-one. The yield of benzoxazinone generally increases as the temperature is raised.
KeywordsChloride Organic Chemistry Pyridine Methoxy Tosyl
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