Synthesis of an s-butyldibenz[a,h]acridine. Alkyl migration in the bernthsen reaction |
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Authors: | L H Klemm Eva Chiang Gerald W O'Bannon |
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Abstract: | The Bernthsen reaction between N-1-naphthyl-2-naphthylamine and 2-methylbutanoic acid and its anhydride at 200–230° for seven hours gives a low yield of 12- or 13-s-butyldibenza,h]acridine, instead of the expected 14-isomer. The parent molecule dibenza,h]acridine results from the same reaction conducted at 270° for thirteen hours. It is suggested that alkyl migration may have occurred in some other cases where the Bernthsen reaction was reported to yield 14-alkyldibenza,h]acridines. |
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