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Amide to nitrile reduction mechanism

  • Page ID
    15021
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    Using cyanuric chloride

    Reaction

    Amide_reduction_cyanuric_chloride_rxn.png

    Mechanism

    Amide_reduction_cyanuric_chloride_mech.png

    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


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