Gould–Jacobs reaction

In the Gould - Jacobs reaction is a name reaction in organic chemistry, which was named after their discoverers Gordon Gould (1920-2005) and Walter Abraham Jacobs ( 1883-1967 ). It is used for the preparation of quinoline derivatives.

Overview reaction

Aniline (or aniline derivatives ) are prepared by reaction with alkoxymethylene malonic acid in a reaction cascade 4- hydroxyquinoline.

Mechanism

Substituted aniline derivative of the alkoxy group of the nucleophile at the electron-deficient C = C double bond of the Methylidenmalonsäureesters Anilinomethylen a malonic acid dialkyl ester, the fused in a Friedel -Crafts reaction, similar to a quinoline. This is hydrolyzed to a quinoline carboxylic acid. The tautomeric β -keto ester decarboxylated to 4- hydroxyquinoline.

An example is the synthesis of 4,7- dichloroquinoline