Synthesis 2007(2): 259-262  
DOI: 10.1055/s-2006-958946
PAPER
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Substitution of Halogens with Amines in 2- and 4-Nitrophenols

Zbigniew Wróbel*, Andrzej Kwast
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6318788.; e-Mail: wrobel@icho.edu.pl;
Further Information

Publication History

Received 11 October 2006
Publication Date:
14 December 2006 (online)

Abstract

Fluorine and chlorine in halonitrophenols are efficiently replaced with alkylamines in acetonitrile or in an excess of the amine at elevated temperature.

    References

  • 1 Terrier F. Nucleophilic Aromatic Displacement - The Influence of the Nitro Group   Feuer H. VCH Publishers; Weinheim: 1991. 
  • 2 Hancock CK. Clague ADH. J. Am. Chem. Soc.  1964,  86:  4942 
  • 3 Castro EA. Saavedra C. Santos JG. Umana MI. J. Org. Chem.  1999,  64:  5401 
  • 4a Reppe W. Justus Liebigs Ann. Chem.  1955,  596:  158 
  • 4b Costerousse G. Cagniant A. Teutsch G. Bull. Soc. Chim. Fr.  1988,  151 
  • 5 Donaghy MJ. Stanford SP. Tetrahedron  1999,  55:  1441 
  • 6 Hodgson HH. Nicholson DE. J. Chem. Soc.  1941,  766 
  • 7 Barlin GB. Ireland SJ. Nguyen TMT. Kotecka B. Rieckmann KH. Aust. J. Chem.  1994,  47:  1553 
  • 8a Cowart M. Kowaluk EA. Daanen JF. Kohlhaas KL. Alexander KM. Wagenaar FL. Kerwin JF. J. Med. Chem.  1998,  41:  2636 
  • 8b Welmaker GS. Nelson JA. Sabalski JE. Sabb AL. Potoski JR. Graziano D. Kagan M. Coupet J. Dunlop J. Mazandarani H. Rosenzweig-Lipson S. Sukoff S. Zhang Y. Bioorg. Med. Chem. Lett.  2000,  10:  1991 
  • 8c Quan ML. Lam PYS. Han Q. Pinto DJP. He MY. Li R. Ellis CD. Clark CG. Teleha CA. Sun J.-H. Alexander RS. Bai S. Luettgen JM. Knabb RM. Wong PC. Wexler RR. J. Med. Chem.  2005,  48:  1729 
  • 9 Magoński J. Pawlak Z. Jasiński T. J. Chem. Soc., Faraday Trans.  1993,  89:  119 
  • 10 Coetzee JF. Padmanabhan GR. J. Am. Chem. Soc.  1965,  87:  5005 
  • 11 Mąkosza M. Sienkiewicz K. J. Org. Chem.  1998,  63:  4199