Lithium aluminium hydride reduces amides to amines
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص236
2025-05-14
548
We’ve talked about reduction of iminium ions formed from carbonyl compounds plus amines. Iminium ions can also be formed by reducing amides with lithium aluminium hydride. A tetrahedral intermediate is formed that collapses to the iminium ion.
The iminium ion is, of course, more electrophilic than the starting amides (amide carbonyl groups are about the least electrophilic of any!), so it gets reduced to the secondary amine. This reaction can be used to make secondary amines from primary amines and acyl chlorides. A similar reduction with lithium aluminium hydride gives a primary amine from a nitrile.
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