10-Hydroxybenzo[h]quinoline

Chemical Properties

Light yellow solid

Uses

5-Hydroxy-4-azaphenanthrene is used to detect boronic acids in reactions and boron containing compounds on solid support. 5-Hydroxy-4-azaphenanthrene is also used as a proton transfer-fluoresence probe to be applied to human serum albumin and beaver apomyoglobin.

Synthesis

10-Bromobenzo[h]quinoline (0.15 mmol, 39 mg) was added to an oven-dried screw-capped vial with carboxylic acid (0.3 mmol), silver carbonate (Ag-based, 0.165 mmol, 22 mg), potassium fluoride (0.15 mmol, 9 mg) and p-xylene (0.5 mL). The reaction mixture was stirred vigorously at 150 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate. Subsequently, the solvent was removed by distillation under reduced pressure and the final product was purified by silica gel column chromatography.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 7, p. 781 - 783
[2] Tetrahedron Letters, 2016, vol. 57, # 7, p. 781 - 783