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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 4, 1974 - Issue 6
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Original Articles

Synthesis of Imines from Aromatic Aldehydes and Aliphatic Amines in Aqueous Solution

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Pages 367-372 | Received 26 Aug 1974, Published online: 05 Dec 2006
 

Abstract

Imines (also called Schiff bases and azomethines) have been of chemical and biological interest for some time.1-4 The formation reaction has been studied extensively and the proposed mechanism includes the presence of a carbinolamine intermediate.

Under most conditions in aqueous solution, equilibrium considerations usually favor the carbonyl and amine as the predominant species. Therefore, imines are usually prepared by direct reaction of liquid amines and aldehydes5,6 or in some appropriate nonaqueous solvent.7,8 Water is then removed during the course of the reaction by means of a drying agent5,6 or a Dean-Stark trap.7,8 Cordes and Jencks9 have shown that imines prepared from certain substituted benzaldehydes and t-butylamine can be isolated from aqueous solution if it is saturated with KOH. In all of the above methods the crude product is purified by distillation.

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