|| Chapter 20: Carboxylic
Acid Derivatives. Nucleophilic Acyl Substitution
Reduction of Nitriles
(for more detail see Chapter 22)
Reactions usually in Et2O or THF followed by H3O+work-up
Reaction type: Nucleophilic Addition
- The nitrile, RC≡N,
gives the 1o amine by conversion of the C≡N to -CH2-NH2
- Nitriles can be reduced by LiAlH4
but NOT the less reactive NaBH4
- Typical reagents : LiAlH4
/ ether solvent followed by aqueous work-up.
- Catalytic hydrogenation (H2
/ catalyst) can also be used giving the same products.
- R may be either alkyl or
|© Dr. Ian Hunt, Department of Chemistry, University