J15- NITRILE to AMINE

By reduction of the appropriate nitrile RC≡N.

• The nitrile is reduced with lithium aluminium hydride (lithal) in dry ether. Li ⁺ [AlH₄] ‾
  CARE: Lithal reacts with damp air to form hydrogen gas – which could cause a small explosion.
  By dissolving the lithal in dry ether this can be significantly reduced.
• The reactants are mixed slowly, with cooling in an ice bath, in a reflux setup, before gently warming under reflux to improve the yield.
• This produces a salt of the amine.
  To liberate the amine from its salt, dilute hydrochloric acid is added.
• The symbol [H] is used to represent the role of the reducing agent.
  CH₃CH₂CN   +   4[H]   →    CH₂CH₂CH₂NH₂
  propanenitrile                    1-aminopropane
• On a large scale, in industry, reduction is achieved using
  hydrogen and nickel catalyst at 200 ^oC.