Chemistry:Skraup reaction

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Skraup reaction
Named after Zdenko Hans Skraup
Reaction type Ring forming reaction
Identifiers
RSC ontology ID RXNO:0000062

The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent such as nitrobenzene to yield quinoline.[1][2][3][4]

The Skraup reaction
The Skraup reaction with substituted aryl

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

Skraup Reaktion glycerin V1-Seite001.svg
Skraub Reaktionsmechanismus V1-Seite001.svg
Skraup quinoline synthesis mechanism.svg

See also

  • Bischler-Napieralski reaction
  • Doebner-Miller reaction

References

  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. http://www.orgsyn.org/demo.aspx?prep=cv1p0478. ; Collective Volume, 1, pp. 478 
  6. Finar, Ivor Lionel (1973). Organic Chemistry, Volume 1 (6th ed.). p. 857. ISBN 978-0582442214.