반응 #634503

반응 방정식

4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

ammonia

sodium carbonate

→

1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine

용매

methanol

methanol

methanol

water

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   농축The mixture was concentrated under reduced pressure
3. 3
   기타to afford a solid
4. 4
   기타The solid was isolated by filtration
5. 5
   세척washed with water
6. 6
   기타purified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane)
7. 7
   기타to provide a white solid
8. 8
   온도at reflux
9. 9
   기타isolated by filtration
10. 10
    세척washed with methanol
11. 11
    기타dried

실험 절차

A suspension of 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline (4.30 g, 11.3 mmol) in a solution of ammonia in methanol (7 M, 43 mL) in a high pressure vessel was heated at 150° C. for 12 hours. The vessel was allowed to cool to room temperature. The mixture was concentrated under reduced pressure to afford a solid that was slurried in water (50 mL), saturated aqueous sodium carbonate, and methanol. The solid was isolated by filtration, washed with water, and purified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane) to provide a white solid. The solid was heated in methanol (200 mL) at reflux, isolated by filtration, washed with methanol, and dried to yield 2.2 g of 1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 261-264° C.

출처