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Quinoline
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== Synthesis == Quinolines are often synthesized from simple anilines using a number of [[name reaction|named reactions]]. ::[[File:Quinoline from aniline.png|400px|class=skin-invert-image]] Going clockwise from top these are: * [[Combes quinoline synthesis]] using [[aniline]]s and β-di[[ketone]]s. * [[Conrad-Limpach synthesis]] using [[aniline]]s and β-ketoesters. * [[Doebner reaction]] using [[aniline]]s with an [[aldehyde]] and [[pyruvic acid]] to form quinoline-4-carboxylic acids * [[Doebner-Miller reaction]] using [[aniline]]s and α,β-unsaturated [[carbonyl]] compounds. * [[Gould-Jacobs reaction]] starting from an aniline and ethyl ethoxymethylenemalonate * [[Skraup synthesis]] using [[ferrous sulfate]], [[glycerol]], [[aniline]], [[nitrobenzene]], and [[sulfuric acid]]. A number of other processes exist, which require specifically substituted anilines or related compounds: * [[Camps quinoline synthesis]] using an o-acylaminoacetophenone and hydroxide * [[Friedländer synthesis]] using [[2-Aminobenzaldehyde|2-aminobenzaldehyde]] and [[acetaldehyde]] * [[Knorr quinoline synthesis]], using a β-ketoanilide and sulfuric acid * [[Niementowski quinoline synthesis]], using anthranilic acid and ketones * [[Pfitzinger reaction]] using an [[isatin]] with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids * [[Povarov reaction]] using an [[aniline]], a [[benzaldehyde]] and an activated [[alkene]] Quinolines are reduced to [[tetrahydroquinoline]]s enantioselectively using several catalyst systems.<ref>Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. ''Chem. Commun.'' '''2005''', 1390.</ref><ref>Reetz, M. T.; Li, X. ''Chem. Commun.'' '''2006''', 2159.</ref> [[File:ImineScope8.png|center|class=skin-invert-image]]
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