Sign In

19.15 : Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.

Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group, both nitro and aldehyde groups will get reduced.

Conversion of the nitro group to the amino group while retaining the aldehydic group can be achieved through acidic reduction using SnCl2, followed by treatment with base.

The reduction of nitrobenzene and its derivatives are useful in industries that manufacture various aniline dyes. This process also has medicinal importance—for example, the synthesis of topical anesthetic benzocaine.

Tags
OximesNitro CompoundsAminesReductionCatalytic HydrogenationHydride ReductionSodium Metal ReductionFeZnSnAcidNitrobenzeneAldehydesAniline DyesBenzocaine

From Chapter 19:

article

Now Playing

19.15 : Preparation of Amines: Reduction of Oximes and Nitro Compounds

Amines

2.9K Views

article

19.1 : Amines: Introduction

Amines

3.8K Views

article

19.2 : Nomenclature of Primary Amines

Amines

3.0K Views

article

19.3 : Nomenclature of Secondary and Tertiary Amines

Amines

3.2K Views

article

19.4 : Nomenclature of Aryl and Heterocyclic Amines

Amines

2.0K Views

article

19.5 : Structure of Amines

Amines

2.2K Views

article

19.6 : Physical Properties of Amines

Amines

2.6K Views

article

19.7 : Basicity of Aliphatic Amines

Amines

5.3K Views

article

19.8 : Basicity of Aromatic Amines

Amines

6.6K Views

article

19.9 : Basicity of Heterocyclic Aromatic Amines

Amines

4.9K Views

article

19.10 : NMR Spectroscopy Of Amines

Amines

7.4K Views

article

19.11 : Mass Spectrometry of Amines

Amines

3.8K Views

article

19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

Amines

2.9K Views

article

19.13 : Preparation of 1° Amines: Azide Synthesis

Amines

3.6K Views

article

19.14 : Preparation of 1° Amines: Gabriel Synthesis

Amines

3.2K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved