Skraup reaction

Short description: Chemical reaction used to synthesize quinolines

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 reactionThe Skraup reaction

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]

## Mechanism

File:Skraup Reaktion glycerin V1.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.). Longman. p. 857. ISBN 978-0582442214.

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