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ChemSpider SyntheticPage 68

Reduction of a nitrile; Preparation of a primary amine using lithium aluminium hydride

SyntheticPage 68 DOI: 10.1039/SP68 Submitted Aug 16, 2001, published Aug 17, 2001 Stephen Caddick (s.caddick@sussex.ac.uk) A contribution from Motherwell Group, University College, London

Chemicals Used
Substrate, Lithium Aluminium Hydride (LAH), Ether, Sodium hydroxide

Procedure
The nitrile (510 mg, 4.76 mmoles) in ether was added to LAH (1.5 g, 39.5 mmoles) in ether (15 ml) and stirred at room temperature overnight. Sodium hydroxide (2.8 ml, 10% solution) was added at 0 o C and after 30 minutes, water (5 ml) was added to give a granular precipitate. The mixture was filtered and the precipitate washed copiously with ether. The combined, washed and dried organic layers were evaporated "in vacuo" to give the product as an oil (292 mg, 55%). .

Author's Comments
Fairly straightforward for a LAH reduction, as always work-up is slightly problematic but this protocol works pretty well. The reaction has only been done a couple of times on this scale and is not optimised. In my experience reductions using LAH can be very dependent on the quality of reagent and sometimes heating is required to force reactions to completion.

Data
5.8, 2H, m, CH; 2.8, 4H, t, CH2NH2; 2.35, 2H, m; 2.0, 1H, m; 1.5, 4H, m;

Lead Reference
For a lead reference see: Rappoport Chemistry of the Cyano Group; Wiley: New York, 1970, pp. 307, 340 Keywords: Cyano, Nitrile , Amine , Reduction, Lithium aluminium hydride , addition, 68
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