Friedländer synthesis

What is Friedländer synthesis?

The Friedländer synthesis is a chemical process that involves the condensation of o-aminobenzaldehydes with compounds containing the structure —CH2CO— to produce quinoline derivatives. This reaction is typically carried out by refluxing an alcoholic solution of the reactants in the presence of dilute caustic.

Friedlander synthesis
Friedländer synthesis

R = H, alkyl, aryl, NO2 , etc.
R’ = H, alkyl, aryl, or COOH

The reaction is of limited use due to the difficulties involved in the preparation of substituted o-aminobenzaldehydes.

References

  • Friedländer, P. (1882), Ueber o-Amidobenzaldehyd. [On o-amidobenzaldehyde.] Ber. Dtsch. Chem. Ges., 15: 2572-2575. https://doi.org/10.1002/cber.188201502219
  • Friedländer, P. and Gohring, C.F. (1883), Ueber eine Darstellungsmethode im Pyridinkern substituirter Chinolinderivate. [On a method of preparation in the pyridine nucleus of substituted quinoline derivatives.] Ber. Dtsch. Chem. Ges., 16: 1833-1839. https://doi.org/10.1002/cber.18830160265
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