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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 12
34
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Original Articles

The Reaction of Diethanolamine with 2-Chloronitrobenzene-A Reinvestigation

Pages 1101-1105 | Published online: 19 Dec 2006
 

Abstract

In a report on the reaction of 2-chloronitrobenzene (1) with diethanolamine (2), Meltsner et al 1 claim that the expected SNAr product, N-(2-nitrophenyl)diethanolamine (3), is not formed; rather that the products are 2,2′-dichloroazobenzene (4), 2-nitrophenol (5), 2-chloroaniline (6) and 4-(2-aminophenyl)morpholine (7). Similar products in which the nitro function is reduced are also reported2 for the corresponding reaction with ethanolamine. In this laboratory, in an attempted preparation of 2,2′-dichloroazobenzene (4) for reference purposes in photochemical studies on the antineoplastic agent 5-(3-azido-4-chlorophenyl)-6-ethyl-pyrimidin-2,4-diamine3, the expected SNAr product (3) was obtained along with other products.

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