Chapter 22: Amines

Reduction of Nitriles

Summary

• The nitrile, RCºN, is reduced to the 1^o amine by conversion of the CºN to R-CH₂-NH₂
• Reagents : either lithium aluminum hydride (LiAlH₄) / ether solvent or catalytic hydrogenation (e.g. H₂/Pd).
• Alkyl nitriles are prepared by nucleophilic substitution (SN2) by cyanide ion, CN^-, of primary or secondary alkyl halides.
• Aryl nitriles can also be reduced to aryl amines.

• What is the oxidation state of the nitrile C in acetonitrile, CH₃CN  ? 
• What is the oxidation of the same C atom in acetonitrile, CH₃CN after reaction with LiAlH₄ ? 

Related reactions

• Reduction of Azides
• Reduction of Nitro compounds
• Reduction of Amides