8-Hydroxyquinoline → HCID 178513320, compound

Participants

Reaction Steps

To 4-cyanobenzoic acid (5 g, 34.0 mmol) in EtOH (150 mL) were added NH2OH.HCl (4.96 g, 71.4 mmol) in water (15 mL) and K2CO3 (7.51 g, 54.4 mmol) in water (30 mL) then 8-hydroxyquinoline (0.064 g, 0.442 mmol). The reaction was stirred at reflux temperature for 4 h. The solvent was removed in vacuo. Water (150 mL) was added and the pH adjusted to 3 using 2M HCl. The white precipitate was filtered off and washed with water to yield E-50734-EXPO37 (3.37 g, 18.71 mmol, 55.0% yield) as a white solid. The mother liquor was extracted with ethyl acetate (75 mL) twice. The combined organics were dried, filtered and condensed in vacuo to obtain: 571 mg (2.54 mmol, 8.0%, 80% purity) as green solid.

Provenance & Evidence