Reaktion #64331

Reaktionsgleichung

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

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

tetrazole

sodium hydride

→

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

Ausbeute 52.2%

Lösungsmittel

dimethylformamide

ethylacetate

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 (30 g)
6. 6
   WaschenElution with 10% to 20% ethylacetatedichloromethane

Vorschrift

A solution of tetrazole (0.17 g) in dimethylformamide (2 ml) at ice-bath temperature under nitrogen was stirred with 60% sodium hydride (0.1 g) for 5 mins and then a solution of 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 14, 0.73 g) in dimethylformamide (8 ml) was added to it. The reaction mixture was stirred at room temperature for 2 hours, diluted with ethylacetate 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 (30 g). Elution with 10% to 20% ethylacetatedichloromethane gave 1-hexyl-3-(1-tetrazolylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone (0.37 g). That this compound was obtained was confirmed by the spectral data: MS: m/e 355 (M+); NMR (CDCl3): δ4.18 (s, 3H, OCH3), 5.68 (s, 2H, CH2), 9,14 (s, 1H, CH= ).

Quelle