Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N-[(2-amino-5-chlorophenyl)phenylmethylene]-1,2-benzenediamine (3), as reported by Kulkarni et al, [1]. Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzo[b,f][1,5]diazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzo[d,h][1,3,6]triazonine (10). Treatment of 5 with PPA, with or without chloroacetic acid, gave [5-chloro-2-[(6-chloro-4-phenyl-2-quinolinyl)amino]phenyl]phenylmethanone (11) as the sole product in 90% yield. Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96% yield, with the exception of 2′-aminoacetophenone (20), which gave a quantitative yield of 2-[((2-acetyl)phenyl)amino]-4-methylquinoline (21). The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed. The structure of 21 was established using high resolution ¹H nmr techniques. Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N-[2-(4-methyl-2-quinolinyl)phenyl]-2-quinolinamine (29) as the major product.

中文翻译：

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5 H-二苯并[ d，h ] [1,3,6]三氮嗪合成的再研究

用邻苯二胺，乙酸钠和乙酸处理5-氯-2-氨基二苯甲酮（1），得到2-（乙酰基）氨基-5-氯二苯甲酮（5）而不是N -[（2-氨基-5-氯苯基） ），如Kulkarni等人[1]报道的那样[]苯基亚甲基] -1,2-苯二胺（3）。正品3制备和与氯乙酸和多磷酸（PPA）处理，得到1，回收3，2,8-二氯-6,12- diphenyldibenzo [ B，F ] [1,5]二氮芳辛（9）和2-氯-6-（氯甲基）-13-苯基-5 H-二苯并[ d，h] [1,3,6]三氮嗪（10）。用PPA在有或没有氯乙酸的情况下处理5，得到的唯一产物为[5-氯-2-[（6-氯-4-苯基-2-喹啉基）氨基]苯基]苯基甲酮（11），产率为90％ 。用乙酸钠和乙酸处理其他二苯甲酮，苯乙酮和苯胺可提供78-96％的乙酰苯胺，但2'-氨基苯乙酮（20）除外，定量得到2-[（（2-乙酰基） ）苯基）氨基] -4-甲基喹啉（21）。讨论了乙酸钠和乙酸形成乙酰苯胺的机理。21的结构是使用高分辨率¹ H nmr技术建立的。尝试准备正宗的由2-氯lepidine（26）和（20）得到21，得到4-甲基-N- [2-（4-甲基-2-喹啉基）苯基] -2-喹啉胺（29）作为主要产物。