Skraup reaction

Skraup reaction

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, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent to yield quinoline.Ref|Skraup1880Ref|Manske1942Ref|Manske1953Ref|Wahren1964

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.Ref|Clark1941

Reaction mechanism

The mechanism is unclear, yet there is good reason to believe that acrolein (obtained by dehydration of glycerol) is an intermediate.

References

# Skraup, Z. H. "Eine Synthese des Chinolins" "Berichte" 1880, "13", 2086-7.
# Manske, R. H. F. "Chem. Rev." 1942, "30", 113. (Review)
# Manske, R. H. F.; Kulka, M. "Org. React." 1953, "7", 80-99. (Review)
# Wahren, M. "Tetrahedron" 1964, "20", 2773. (Review)
# Clarke, H. T.; Davis, A. W. “Quinoline” Organic Syntheses Collective Volume 1, page 478 (1941). http://www.orgsyn.org/orgsyn/pdfs/CV1P0478.pdf.

ee also

* Bischler-Napieralski reaction
* Doebner-Miller reaction


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