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[edit]

References[edit]

  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. 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.
  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.; Collective Volume, 1, p. 478
  6. ^ Finar, Ivor Lionel (1973). Organic Chemistry, Volume 1 (6th ed.). p. 857. ISBN 978-0582442214.