8-Hydroxyquinoline → HCID 44553783, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzyl-2-chloroisonicotinamide (1.00 g, 4.06 mmol), copper iodide(I) (0.12 g, 0.61 mmol), 8-hydroxyquinoline (0.09 g, 0.61 mmol), potassium carbonate (0.84 g, 6.09 mmol), 4-(benzyloxy)pyridin-2(1H)-one (0.82 g, 4.06 mmol) in N,N-dimethylormamide (20 mL) was heated to 110° C. for 16 hours under nitrogen atmosphere and concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with water (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with 60-75% ethyl acetate in petroleum ether to give 4-benzyloxy-2-oxo-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as colorless solid (0.89 g, 53%): mp 158-161° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.60 (d, J=5.0 Hz, 1H), 8.19 (s, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.74 (d, J=5.0 Hz, 1H), 7.42-7.26 (m, 11H), 6.16-6.13 (m, 1H) 5.95 (d, J=2.3 Hz, 1H), 5.02 (s, 2H), 4.58 (d, J=5.6 Hz, 2H); MS (ES+) m/z 412.2 (M+1).

Provenance & Evidence