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Synthesis 2003(5): 0681-0684
DOI: 10.1055/s-2003-38069
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of N-Benzhydrylamides from Nitriles by Ritter Reactions in Formic Acid

Glen C. Gullickson, David E. Lewis*
Department of Chemistry, University of Wisconsin - Eau Claire, Eau Claire WI 54702-4004, USA
Fax: +1(715)8364979; e-Mail: lewisd@uwec.edu;
Further Information

Publication History

Received 27 November 2002
Publication Date:
21 March 2003 (online)

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Abstract

Benzhydrol reacts with nitriles in refluxing formic acid to produce amides arising from the Ritter reaction. This reaction does not require a strong acid catalyst, and the products are isolated without the need for chromatography. The conditions permit the preparation of acrylamides and methacrylamides without polymerization of the nitrile.

Key Words

Ritter reaction - alcohols - carboxylic acids - nitriles - amides

    References

  • 1 Review: Krimer LI. Cota D. Org. React.  1969,  17:  213 
    Google Scholar
  • 2 Review: Bishop R. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Fleming I. Winterfeldt E. Pergamon; Oxford: 1991.  p.261-300  
    Google Scholar
  • 4 Cheeseman GWH. Chem. Ind. (London, U.K.)  1954,  281 
    Google Scholar
  • 5 Cheeseman GWH. Poller RC. Analyst (Cambridge, U.K.)  1962,  87:  366 
    CrossrefGoogle Scholar
  • 6 Okada T. Saeki K. Kawanisi M. Nozaki H. Tetrahedron  1970,  26:  3661 
    CrossrefGoogle Scholar
  • 7 Davies W. Ramsay TH. Stove ER. J. Chem. Soc.  1949,  2633 
    Google Scholar
  • 8 Sanguigni JA. Levins R. J. Med. Chem.  1964,  7:  573 
    Google Scholar
  • 9 Loev B. Chem. Ind. (London, U.K.)  1964,  193 
    Google Scholar
  • 10 Koch H. Haaf W. Org. Synth., Coll. Vol. 5   Wiley; London: 1973.  p.20-22  
    Google Scholar
  • 11 Haaf W. Org. Synth., Coll. Vol. 5   Wiley; London: 1973.  p.739-742  
    Google Scholar
  • 12 Guyot A. Kovache A. Comptes Rend. Hebd.  1912,  154:  121 
    Google Scholar
  • 13 Kovache A. Ann. Chim.  1918,  10:  184 
    Google Scholar
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Gullickson, G. C.; Lewis, D. E. Aust. J. Chem., 2003, 56, accepted for publication.