Imidazole → 1-hexyl-3-(1H-imidazol-1-ylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone

Participants

Reaction Steps

A solution of imidazole (0.07 g) in dimethylformamide (1.5 ml) was stirred with 60% sodium hydride (0.04 g) at ice-bath temperature under nitrogen until the reaction was complete. The reaction mixture was then treated with a solution of 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 14, 0.27 g) in dimethylformamide (3 ml) and stirred at room temperature for 2 hours. The solution was then diluted with ethyl acetate and washed several times with water. The organic layer was then dried and evaporated under reduced pressure. The crude reaction product was chromatographed on silica-gel (44 g). Elution with 2% methanoldichloromethane gave 1-hexyl-3-(1H-imidazol-1-ylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone which crystallized as a white solid. That the expected product was obtained was confirmed by the spectral data: MS: m/e 353 (M.+); NMR (CDCl3): δ3.90 (s, 3H, OCH3), 5,18 (s, 2H, CH2 -Im), 6.99, 7.14, 7.72 (s, 3H, CH=) wherein Im represents imidazole.

Provenance & Evidence