Bernthsen acridine synthesis

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The Bernthsen acridine synthesis is the chemical reaction of a diarylamine heated with a carboxylic acid (or acid anhydride) and zinc chloride to form a 9-substituted acridine. [1] [2]

The Bernthsen acridine synthesis Bernthsen Acridine Synthesis Scheme.png
The Bernthsen acridine synthesis

Using zinc chloride, one must heat the reaction to 200-270 °C for 24hrs. [3] The use of polyphosphoric acid will give acridine products at a lower temperature, but also with decreased yields.

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References

  1. Bernthsen, A.; Ann.1878, 192, 1.
  2. Bernthsen, A.; Ann.1884, 224, 1.
  3. Popp, F. D. J. Org. Chem. 1962, 27, 2658. ( doi : 10.1021/jo01054a518)