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Synthesis 1989; 1989(4): 312-313
DOI: 10.1055/s-1989-27238
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An Improvement of the N-Arylation of Amides; Application to the Synthesis of Substituted 3-(N-Acetyl-N-phenylamino)-pyridines

Alfred Greiner*
  • *Rhone-Poulenc Agrochimie, La Dargoire Research Center, 14 -20 rue Pierre Baizet, F-69009 Lyon, France
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Publikationsdatum:
17. September 2002 (online)

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In the presence of catalytic quantities of tris(3,6-dioxaheptyl)amine (TDA-1) and of copper(I) chloride, with azeotropic separation of the reaction water, the N-arylation of carboxamides has been simplified and can now be performed under rather mild conditions, using substituted bromobenzenes as arylating agents in quasi-stoichiometric quantities in boiling xylene, or using chlorobenzenes as arylating agents and as reaction solvents at reflux. The general applicability of the reaction to the preparation of various diarylamines is demonstrated.