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Gould–Jacobs reaction

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Gould–Jacobs reaction

The Gould–Jacobs reaction is an organic synthesis for the preparation of quinolines (more specifically, a 4-Quinolinol). 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.

Further reading:

Examples

An example is the synthesis of 4,7-dichloroquinoline

  • Floctafenine and Glafenine are a pair of fenamate NSAIDs whose synthesis rely on the Gould–Jacobs reaction.
  • A lot of quinolone antibiotic structures such as Rosoxacin, Oxolinic acid, Droxacin, etc.

    • References

    Gould–Jacobs reaction Wikipedia
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