Prepare imine from aniline

Synthesis following imine from aniline. You can use only use following compounds as reagents.

imine

NaNO2, dilute HCl, LiAlH4, PCC, ether, H2O, KCN

How to prepare imine compounds?

Imines are prepared by the reaction of carbonyl compound (aldehyde or ketone) and primary amine such as methanamine, aniline. A water molecule is eliminated in this reaction when imine is given.


In this question, our target is synthesis an amine compound from aniline.

aniline to imine

Steps of preparing imine

  1. Aniline is a primary amine. Therefore we have to only prepare carbonyl compound (aldehyde or ketone).
  2. Now, we can understand carbonyl compound should be benzaldehyde.

Aniline and benzaldehyde reaction

Aniline is a promary amine compound and benzaldehye is an aldehyde. In the reaction, two hydrogens of aniline (in -NH2) and oxygen atom which is connected to the carbonyl carbon are eliminated as a water molecule to give imine.

aniline and benzaldehyde reaction

Complete conversion of imine preparing

preparing imine from aldehyde and primary amine