Gould-Jacobs reaction

Gould-Jacobs reaction

The Gould-Jacobs reaction is an organic synthesis for the preparation of quinolines ["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
] . 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.

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An example is the synthesis of 4,7-dichloroquinoline [Organic Syntheses, Coll. Vol. 3, p.272 (1955); Vol. 28, p.38 (1948). [http://www.orgsynth.org/orgsyn/pdfs/CV3P0272.pdf Link] ]

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