HCID 22395292, compound → HCID 22395290, compound

Participants

Reaction Steps

A suspension of N-{2-[(E)-2-phenylethenyl]-4-quinolinyl}acetamide (1.00 g, 3.5 mmol) in 6 N hydrochloric acid (10 mL) was stirred at reflux for 4 h. After cooling to ambient temperature and stirring for 18 h, the solid was collected by filtration. The solid was treated with 10% ammonium hydroxide solution (60 mL) by stirring at ambient temperature overnight, then extracted with ethyl acetate (30 mL). The ethyl acetate layer was separated, washed with water (50 mL), brine (20 mL), dried over Na2SO4, filtered, and the solvent remove in vacuo to provide the title compound as a yellow-orange solid (0.72 g, 84%). MS (API+): M+1: 247 (100%); 1H NMR (300 MHz, DMSO-d6) d 6.79 (br s, 2H, exchangeable), 6.81 (s, 1H), 7.26 (d, J=16.2 Hz, 1H), 7.30-7.46 (m, 4H), 7.55-7.61 (m, 1H), 7.62 (d,J=16.2 Hz, 1H), 7.67-7.73 (m, 2H), 7.77 (d, J=8.4 Hz, 1H), 8.12 (d, J=8.5 Hz, 1H).

Provenance & Evidence