Promoting the usability of online AMIA Symposium Proceedings

George R Kim1, Caroline Zambrowicz, Dongming Zhang

  • 1Division of Health Sciences Informatics, Johns Hopkins University School of Medicine, Baltimore, MD, USA.

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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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Preparation of Amines: Reduction of Amides and Nitriles

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Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...