Pinner reaction

What is Pinner reaction?

Pinner reaction, also known as Pinner ortho-ester synthesis or Pinner amidine synthesis, is the formation of imino esters (alkyl imidates) by addition of dry hydrogen chloride to a mixture of a nitrile and an alcohol. Treatment of alkyl imidates with ammonia or primary or secondary amines affords amidines, while treatment with alcohols yields ortho-esters.

Pinner reaction - Pinner ortho-ester synthesis -Pinner amidine synthesis
Pinner reaction

References

  • Pinner, A. and Klein, F. (1877), Umwandlung der Nitrile in Imide. [Conversion of nitriles to imides.] Ber. Dtsch. Chem. Ges., 10: 1889-1897. https://doi.org/10.1002/cber.187701002154
  • Pinner, A. and Klein, F. (1878), Umwandlung der Nitrile in Amide. [Conversion of nitriles to amides.] Ber. Dtsch. Chem. Ges., 11: 4-11. https://doi.org/10.1002/cber.18780110103
  • Pinner, A. and Klein, F. (1878), Umwandlung der Nitrile in Imide. [Conversion of nitriles to imides.] Ber. Dtsch. Chem. Ges., 11: 1475-1487. https://doi.org/10.1002/cber.18780110258
  • Pinner, A. (1883), Ueber die Umwandlung der Nitrile in Imide. Verhalten der Blausäure und des Aethylencyanids gegen Salzsäure und Alkohol. [On the conversion of nitriles into imides. Behavior of hydrocyanic acid and ethylene cyanide against hydrochloric acid and alcohol.] Ber. Dtsch. Chem. Ges., 16: 352-363. https://doi.org/10.1002/cber.18830160187
  • Pinner, A. (1883), Ueber die Umwandlung der Nitrile in Imide. [On the conversion of nitriles to imides.] Ber. Dtsch. Chem. Ges., 16: 1643-1655. https://doi.org/10.1002/cber.18830160235
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