Pinner reaction
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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]]