Reaktion #64330

Reaktionsgleichung

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

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

1,2,4-triazole

sodium hydride

→

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

Ausbeute 80.0%

Lösungsmittel

dimethylformamide

ethyl acetate

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed several times with water
2. 2
   SonstigeThe organic layer was dried
3. 3
   Sonstigeevaporated under reduced pressure
4. 4
   SonstigeThe resulting crude reaction product
5. 5
   Sonstigewas chromatographed on silica-gel (4 g)
6. 6
   WaschenElution with 2.5% methanol-ethyl acetate

Vorschrift

A solution of 1,2,4-triazole (0.033 g) in dimethylformamide (0.7 ml) was stirred at ice-bath temperature with 60% sodium hydride (0.02 g) for 10 mins under nitrogen and then a solution of 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 14, 0.14 g) in dimethylformamide (1.7 ml) was added to it. The mixture was stirred at room temperature for 2 hours, then diluted with ethyl acetate and then washed several times with water. The organic layer was dried and evaporated under reduced pressure. The resulting crude reaction product was chromatographed on silica-gel (4 g). Elution with 2.5% methanol-ethyl acetate gave 1-hexyl-3-(1,2,4-triazol-1-ylmethyl)-4-methoxy-6-methyl-2(1 H)-quinolinone as white crystals (80%). That the expected product was obtained was confirmed by the spectral data: MS: m/e 354 (M+); NMR (CDCl3): δ4.15 (s, H, OCH3), 5.42 (s, 2H, CH2), 7.86, 8.5 (s, 2H, CH=).

Quelle