Amide to Nitrile Reduction
- Page ID
- 22640
\( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)
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.