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Ritter reaction

The Ritter reaction is a chemical reaction that transforms a nitrile into a N-alkyl amide using various alkylating reagents, for example, strong acid and isobutylene.^[1]^[2]^[3]

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Primary^[4], secondary^[5], tertiary^[6], and benzylic^[7] alcohols, as well as tert-butyl acetate^[8], also successfully react with nitriles in the presence of strong acids to form amides via the Ritter reaction.

Reaction mechanism

The Ritter reaction proceeds by the electrophilic addition of either the carbenium ion 2 or covalent species^[9]^[10] to the nitrile. The resulting nitrilium ion 3 is hydrolyzed by water to the desired amide 5.

References

^ Ritter, J. J., Minieri, P. P.; J. Am. Chem. Soc. 1948, 70, 4045.
^ Ritter, J. J., Kalish, J.; J. Am. Chem. Soc. 1948, 70, 4048.
^ Krimen, L. I., Cota, D. J.; Org. React. 1969, 17, 213-325. (Review)
^ Lebedev, M. Y., Erman, M. B.; Tetrahedron Lett. 2002, 43, 1397-1399. (Article)
^ Bishop, R.; In Comp. Org. Synth.; Trost, B.M., Fleming, I.; Eds.; Pergamon Press: New York, 1992; Vol. 6, 261-300. (Review)
^ Ritter, J. J., Kalish, J.; Organic Syntheses, Coll. Vol. 5, p.471 (1973); Vol. 44, p.44 (1964). (Article)
^ Parris, C. L.; Organic Syntheses, Coll. Vol. 5, p.73 (1973); Vol. 42, p.16 (1962). (Article)
^ Fernholz, H., Schmidt, H.J.; Angew. Chem., Int. Ed. Eng., 1969, 8, 521. (Article)
^ Booth, B.L., Jibodu, K.O., Proenca, F.J.R.P.; J. Chem. Soc., Perkin Trans. 1, 1983, 1067 - 1073, (Article)
^ Martínez, A.G., Alvarez, R.M., Vilar, E.T., Fraile, A.G., Hanack ,M., Subramanian, L. R.; Tetrahedron Lett. 1989, 30, 581-582. (Article)