Reaktion #64329

Reaktionsgleichung

1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

1Hexyl-3-Bromomethyl-4-Methoxy-6-Methyl-2(1H)-Quinolinone

imidazole

sodium hydride

→

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

Lösungsmittel

dimethylformamide

ethyl acetate

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed several times with water
2. 2
   SonstigeThe organic layer was then dried
3. 3
   Sonstigeevaporated under reduced .pressure
4. 4
   SonstigeThe crude reaction product
5. 5
   Sonstigewas chromatographed on silica-gel (44 g)
6. 6
   WaschenElution with 2% methanoldichloromethane

Vorschrift

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.

Quelle