23.2: Preparation of Amines - A Review
- Page ID
- 89812
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Reduction of Other Functional Groups that Contain Nitrogen
Reduction of Nitro Groups
Several methods for reducing nitro groups to amines are known. These include catalytic hydrogenation (H2 + catalyst), zinc or tin in dilute mineral acid, and sodium sulfide in ammonium hydroxide solution. The procedures described above are sufficient for most case
Nitriles can be converted to 1° amines by reaction with LiAlH4
During this reaction the hydride nucleophile attacks the electrophilic carbon in the nitrile to form an imine anion. Once stabilized by a Lewis acid-base complexation the imine salt can accept a second hydride to form a dianion. The dianion can then be converted to an amine by addition of water.
