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Gould-Jacobs reaction
Introduction
The Gould-Jacobs reaction is an organic synthesis for the preparation of quinolines [1]. In this reaction aniline or an aniline derivative first reacts with malonic acid derivative ethyl ethoxymethylenemalonate with substitution of the ethoxy group by nitrogen. A benzannulation takes place by application of heat to a quinoline. The ester group is hydrolysed by sodium hydroxide to the carboxylic acid and decarboxylation again by application of heat to 4-hydroxyquinoline.
An example is the synthesis of 4,7-dichloroquinoline [2]
References
- ↑ The Synthesis of Certain Substituted Quinolines and 5,6-Benzoquinolines R. Gordon Gould, , Walter Abraham Jacobs J. Am. Chem. Soc.; 1939; 61(10); 2890-2895. doi:10.1021/ja01265a088
- ↑ Organic Syntheses, Coll. Vol. 3, p.272 (1955); Vol. 28, p.38 (1948). Link