Skraup reaction

{{Reactionbox

| Name = Skraup reaction

| Type = Ring forming reaction

| NamedAfter = Zdenko Hans Skraup

| Section3 = {{Reactionbox Identifiers

| RSC_ontology_id = 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.{{cite journal | author = Skraup, Z. H. | title = Eine Synthese des Chinolins | journal = Berichte | year = 1880 | volume = 13 | pages = 2086}}{{cite journal | author = Manske, R. H. F. | journal = Chem. Rev. | year = 1942 | volume = 30 | pages = 113–144 | doi = 10.1021/cr60095a006 | title = The Chemistry of Quinolines.}}{{cite journal | last1=Manske | first1=Richard H. F. |last2=Kulka | first2=Marshall | journal = Org. React. | year = 1953 | volume = 7 | pages = 80–99 | title = The Skraup Synthesis of Quinolines | doi = 10.1002/0471264180.or007.02| isbn=0471264180 }}{{cite journal | author = Wahren, M. | journal = Tetrahedron | year = 1964 | volume = 20 | pages = 2773 | doi = 10.1016/S0040-4020(01)98495-9 | title = Stabilisotop markierte verbindungen—II, Untersuchung der skraupschen chinolin-synthese mit hilfe von 15N | issue = 12}}

Image:Skraup Reaktion overview V1-Seite001.svg

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.{{OrgSynth | author = Clarke, H. T.; Davis, A. W. | title = Quinoline | collvol = 1 | collvolpages = 478 | year = 1941 | prep = cv1p0478}} Arsenic acid may be used instead of nitrobenzene and the former is better since the reaction is less violent.{{cite book | last1=Finar | first1=Ivor Lionel | title=Organic Chemistry, Volume 1 | page=857 | edition=6th | year=1973 | publisher=Longman | isbn=978-0582442214}}