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Amide to Nitrile Reduction

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

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

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