反应详情

The 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (2.29 g, 0.01 mole), was added to a suspension of sodium hydride (0.44 g of 60% of sodium hydride/oil, 0.01 mole, washed one with hexanes) in 50 ml of dimethylformamide. The mixture was heated to 70° C. for 1 hr before the addition of chloroacetone (0.93 g, 0.01 mole) at room temperature. The reaction mixture was stirred at room temperature overnight, then poured into 300 ml of water. The precipitate was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight. The solid was recrystallized from methanol-water and dried under high vacuum at 50° C. overnight. The solid was dissolved in methanol, treated with charcoal, and filtered through Celite to give a pale yellow filtrate. The filtrate was concentrated and diluted with water to initiate crystallization. The precipitate was collected by filtration, washed with water, and dried under high vacuum overnight. The solid was dissolved in isopropyl alcohol, acidified with ethereal hydrogen chloride, diluted with isopropyl ether, and seeded to initiate crystallization. The crystalline solid was collected by filtration, washed with isopropyl ether, and dried under high vacuum overnight to give 1.6 g, (50%), m.p. 220°-22° C.

1. filtrationThe precipitate was collected by filtration
2. washwashed with water
3. customdried under high vacuum at 50° C. overnight
4. customThe solid was recrystallized from methanol-water
5. customdried under high vacuum at 50° C. overnight
6. dissolutionThe solid was dissolved in methanol
7. additiontreated with charcoal
8. filtrationfiltered through Celite
9. customto give a pale yellow filtrate
10. concentrationThe filtrate was concentrated
11. additiondiluted with water
12. customcrystallization
13. filtrationThe precipitate was collected by filtration
14. washwashed with water
15. customdried under high vacuum overnight
16. dissolutionThe solid was dissolved in isopropyl alcohol
17. additiondiluted with isopropyl ether
18. customcrystallization
19. filtrationThe crystalline solid was collected by filtration
20. washwashed with isopropyl ether
21. customdried under high vacuum overnight
22. customto give 1.6 g, (50%), m.p. 220°-22° C.