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19.16 : Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.

Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe, Zn, Ni, and strong reducing agents like lithium aluminum hydride. The reaction introduces only the amino group without extending the carbon skeleton.

Amide reduction is useful in the last step of monoalkylation of arylamines.

Figure1

Tags
AminesReductionAmidesNitrilesReducing AgentsLithium Aluminum HydrideCatalytic HydrogenationAmino GroupAlkyl HalidesSodium CyanideSN2 MechanismPrimary AminesSecondary AminesTertiary AminesMonoalkylationArylamines

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19.16 : Preparation of Amines: Reduction of Amides and Nitriles

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19.1 : Amines: Introduction

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19.2 : Nomenclature of Primary Amines

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19.3 : Nomenclature of Secondary and Tertiary Amines

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19.4 : Nomenclature of Aryl and Heterocyclic Amines

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19.5 : Structure of Amines

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19.6 : Physical Properties of Amines

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19.7 : Basicity of Aliphatic Amines

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19.8 : Basicity of Aromatic Amines

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19.9 : Basicity of Heterocyclic Aromatic Amines

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19.10 : NMR Spectroscopy Of Amines

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19.11 : Mass Spectrometry of Amines

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19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

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19.13 : Preparation of 1° Amines: Azide Synthesis

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19.14 : Preparation of 1° Amines: Gabriel Synthesis

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