Pinner reaction

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 additions. [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 ] [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 ] [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 ] [Roger. R.; Neilson, D. "Chem. Rev." 1961, "61", 179-211. (Review, DOI|10.1021/cr60210a003)]

These salts can react with an excess of alcohol to form the orthoester RC(OR)₃, with ammonia or an amine to form an amidine or with water to form an ester.

IUPAC Nomenclature for Transformations: Alkoxy,oxo-de-nitrilo-tersubstitution, another name for this reaction is nitrile alcoholysis.

References