Uses
2-Chloroquinoline-3-Boronic acid can be converted to 2-chloro-3-hydroxyquinoline in 98% yield by oxidizing with ammonium chloride in aqueous solution with peroxide. Further hydrolysis of 2-chloro-3-hydroxyquinoline yields 3-hydroxy-2-quinolinone.
Synthesis
2-Chloroquinoline was lithiated with lithium diisopropylamide in a low-temperature tetrahydrofuran solution, followed by the addition of trimethylborate ester, and finally acidification to obtain 2-Chloroquinoline-3-boronic acid in 85% yield.
References
[1] Marsais, F., Godard, A., & Queguiner, G. (1989). Directed ortho-lithiation of chloroquinolines. Application to synthesis of 2,3-disubstituted quinolines.
Journal of Heterocyclic Chemistry,
26 6, 1589–1594.
https://doi.org/10.1002/jhet.5570260615
