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Synthesis 1997; 1997(1): 87-90
DOI: 10.1055/s-1997-1505
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Lewis Acid Catalyzed Reaction of Cinnamanilides: Competition of Intramolecular and Intermolecular Friedel-Crafts Reaction

Tai-Chi Wang1 , Yeh-Long Chen2 , Kuan-Han Lee3 , Cherng-Chyi Tzeng4
  • 1School of Chemistry, Kaohsiung Medical College, Kaohsiung City 807, Taiwan, R.O.C.; Department of Pharmacy, Tajen Junior College of Pharmacy, Pingtung, Taiwan, R.O.C.
  • 2School of Chemistry, Kaohsiung Medical College, Kaohsiung City 807, Taiwan, R.O.C.
  • 3Department of Pharmacy, Tajen Junior College of Pharmacy, Pingtung, Taiwan, R.O.C.
  • 4School of Chemistry, Kaohsiung Medical College, Kaohsiung City 807, Taiwan, R.O.C., Fax +886(7)3125339
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Publication Date:
31 December 2000 (online)

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The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum(III) chloride in chlorobenzene at 120°C or in benzene at 80°C afforded exclusively 6-hyddroxyquinolin-2(1H)-one (3a) or 4‘-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum(III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.

Treatment of cinnamanilide with AlCl3 in chlorobenzene at 120°C or in benzene at 80°C afforded exclusively quinolin-2(1H)-one or 3-3-diphenylpropionanilide, respectively