Amide to Nitrile Reduction

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Reaction

Mechanism

Notes

Conditions are relatively mild: dimethylformamide at room temperature.
Compatible with most sensitive functionalities.
Only one third molar equivalent of cyanuric chloride is needed to go to completion.
Cyanuric chloride should be recrystallized before use.
The excess cyanuric chloride and the cyanuric acid by-product can be removed by 5% aq.sodium bicarbonate washings.

References

Olah, G.A.; Narang, S.C.; Fung, A.P.; Gupta, B.G.B. Synthesis, 1980, 657.
Chakrabarti, J. K.; Hotten, T. J. Chem. Soc., Chem. Commun., 1972, 1226.
Maetz, P.; Rodriguez, M. Tetrahedron Lett. 1997, 38, 4221.

Contributors

OChemOnline

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