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Skraup reaction

From Wikipedia, the free encyclopedia
Skraup reaction
Named afterZdenko Hans Skraup
Reaction typeRing forming reaction
Identifiers
RSC ontology IDRXNO:0000062

TheSkraup synthesis is achemical reaction used to synthesizequinolines. It is named after the Czech chemistZdenko Hans Skraup (1850–1910). In the archetypal Skraup reaction,aniline is heated withsulfuric acid,glycerol, and anoxidizing agent such asnitrobenzene to yield quinoline.[1][2][3][4]

The Skraup reaction
The Skraup reaction

In this example,nitrobenzene serves as both thesolvent and the oxidizing agent. The reaction, which otherwise has a reputation for being violent, is typically conducted in the presence offerrous sulfate.[5]Arsenic acid may be used instead of nitrobenzene and the former is better since the reaction is less violent.[6]

Mechanism

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See also

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References

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  1. ^Skraup, Z. H. (1880). "Eine Synthese des Chinolins".Berichte.13: 2086.
  2. ^Manske, R. H. F. (1942). "The Chemistry of Quinolines".Chem. Rev.30:113–144.doi:10.1021/cr60095a006.
  3. ^Manske, Richard H. F.; Kulka, Marshall (1953). "The Skraup Synthesis of Quinolines".Org. React.7:80–99.doi:10.1002/0471264180.or007.02.ISBN 0471264180.
  4. ^Wahren, M. (1964). "Stabilisotop markierte verbindungen—II, Untersuchung der skraupschen chinolin-synthese mit hilfe von 15N".Tetrahedron.20 (12): 2773.doi:10.1016/S0040-4020(01)98495-9.
  5. ^Clarke, H. T.; Davis, A. W. (1941)."Quinoline".Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link);Collected Volumes, vol. 1, p. 478.
  6. ^Finar, Ivor Lionel (1973).Organic Chemistry, Volume 1 (6th ed.). Longman. p. 857.ISBN 978-0582442214.
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