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Further Information

Related Reactions
Synthesis of amidines
Synthesis of iminoethers
Synthesis of thionoesters

Pinner Reaction

The Pinner Reaction is the partial solvolysis of a nitrile to yield an iminoether. Treatment of the nitrile with gaseous HCl in a mixture of anhydrous chloroform and an alcohol produces the imino ether hydrochloride. These salts are known as Pinner Salts, and may react further with various nucleophiles.

Mechanism of the Pinner Reaction

(or amines instead of NH3)

Recent Literature

Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Synthesis of Amidines
S. Caron, L. Wei, J. Douville, A. Ghosh, J. Org. Chem., 2010, 75, 945-947.

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
K. Hyodo, G. Hasegawa, H. Maki, K. Uchida, Org. Lett., 2019, 21, 2818-2822.