Pinner reaction 176619 221673991 2008-06-25T15:48:21Z Chem-awb 4806773 [[Category:Name reactions]] using [[Project:AutoWikiBrowser|AWB]] The '''Pinner reaction''' (after [[Adolf Pinner]]) is an [[organic reaction]] of a [[nitrile]] with an [[alcohol]] under [[acid]] [[catalysis]] for instance [[hydrochloric acid]]. The product formed is the hydrochloric acid salt of an [[imino ester]] or an [[alkyl]] [[imidate]], which sometimes is called a '''Pinner salt'''. The reaction is a sequence of [[nucleophilic addition]]s.<ref>{{cite journal | title = Umwandlung der Nitrile in Imide | author = A. Pinner, F. Klein | journal = [[Berichte der deutschen chemischen Gesellschaft]] | volume = 10 | issue = 2 | pages = 1889–1897 | year = 1877 | url = | doi = 10.1002/cber.187701002154 }}</ref><ref>{{cite journal | title = Umwandlung der Nitrile in Imide | author = A. Pinner, Fr. Klein | journal = [[Berichte der deutschen chemischen Gesellschaft]] | volume = 11 | issue = 4 | pages = 1475–1487 | year = 1878 | url = | doi = 10.1002/cber.18780110258 }}</ref><ref>{{cite journal | title = Ueber die Umwandlung der Nitrile in Imide | author = A. Pinner | journal = [[Berichte der deutschen chemischen Gesellschaft]] | volume = 16 | issue = 2 | pages = 1643–1655 | year = 1883 | url = | doi = 10.1002/cber.18830160235 }}</ref><ref>Roger. R.; Neilson, D. ''[[Chem. Rev.]]'' '''1961''', ''61'', 179-211. (Review, {{DOI|10.1021/cr60210a003}})</ref> These salts can react with an excess of alcohol to form the [[orthoester]] RC(OR)<sub>3</sub>, with [[ammonia]] or an [[amine]] to form an [[amidine]] or with water to form an [[ester]]. [[image:Reaction-pinner2.png|center]] [[IUPAC Nomenclature for Transformations]]: Alkoxy,oxo-de-nitrilo-tersubstitution, another name for this reaction is '''nitrile alcoholysis'''. ==References== {{Reflist}} [[Category:Addition reactions]] [[fr:Réaction de Pinner]] [[Category:Name reactions]]