6-Bromo-2(1H)-quinolone

Chemical Properties

Beige Solid

Uses

6-Bromo-2(1H)-quinolinone is a useful intermediate for the synthesis of other quinoline derivatives.

Synthesis

General procedure for the synthesis of 6-bromoquinolin-2(1H)-one from the compound (CAS:327058-51-5): 6-bromo-2(1H)-quinolinone (6.0 g, 22.2 mmol) was dissolved in concentrated H2SO4 (30 mL) and the reaction was heated in an oil bath at 100 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and quenched with ice water. The precipitate precipitated was collected by filtration, washed with water and subsequently dried under vacuum to afford 6-bromoquinolin-2(1H)-one as a white solid (4.8 g, 97% yield). Mass spectrum (ES+) m/e 225 [M+H]+.

References

[1] Patent: WO2006/132739, 2006, A2. Location in patent: Page/Page column 35-36
[2] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 508 - 518
[3] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 306 - 311