Phenol → HCID 32388, compound

Participants

Reaction Conditions

Reaction Steps

Cupric oxide (0.2 g) was added in one portion to a mixture of phenol (2 g, 21 mmol), potassium carbonate (2.7 g, 20 mmol), and 5-bromoisoquinoline (2.1 g, 10 mmol) in pyridine (20 ml) heated at 90° C. under nitrogen. The mixture was then heated at 140° C. for 18 h. After this time the pyridine was removed in vacuo, the residue suspended in ether and the mixture filtered through a pad of silica gel. The solvent was evaporated and the residue purified by column chromatography on silica with ethyl acetate/hexane (1:3-1:1) as eluant to give the title compound as a colourless solid (1.1 g, 49%); δH (CDCl3) 7.1-7.5 (7H, m, ArH), 7.75 (1H, d, J 8 Hz, ArH), 8.02 (1H, d, J 8 Hz, ArH), 8.57 (1H, d, J 8 Hz, ArH), and 9.3 (1H, s, 1-H).

Provenance & Evidence