반응 #607455

반응 방정식

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

2-Furyl-1H-Imidazo[4,5-c]quinoline

용매

pyridine

NaOH

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   기타the solvent was evaporated under reduced pressure
4. 4
   기타to afford an orange solid
5. 5
   온도After cooling on ice the pH
6. 6
   기타The solid that precipitated
7. 7
   여과was filtered off
8. 8
   세척washed with water and ether
9. 9
   추출Then extracted with ethyl acetate (3 times 15 ml)
10. 10
    세척washed with water (3 time 15 ml)
11. 11
    건조dried over MgSO4
12. 12
    기타The solvent was evaporated
13. 13
    기타the residue was dried

실험 절차

2-Furoyl chloride (1.1 g, 0.8 ml, 8.1 mmol) in dry dichloromethane (15 ml) was added dropwise to a solution of to 3,4-diaminoquinoline 8 (1.0 g, 6.0 mmol) in dry pyridine (6.2 ml) under nitrogen. The solution was stirred for 2 hours at room temperature. Water (15 ml) was added to quench the reaction and the solvent was evaporated under reduced pressure to afford an orange solid. This crude solid in 2N NaOH (15 ml) was refluxed for 2 hours. After cooling on ice the pH was adjusted to 7 using concentrated HCl. The solid that precipitated was filtered off and washed with water and ether. Then extracted with ethyl acetate (3 times 15 ml) and washed with water (3 time 15 ml) and dried over MgSO4. The solvent was evaporated and the residue was dried. Eluent for column chromatography was 1-5% methanol in dichloromethane. Yield: 0.62 g (44%). Mp.: 236-238° C. 1H NMR (DMSO-d6): δ 6.74 (s, 1H, Ar); 7.35 (d, 1H, J=3.7 Hz, Ar); 7.69-7.73 (m, 2H, Ar); 7.83 (s, 1H, Ar); 8.09 (s, 1H, Ar); 8.46 (s, 1H, Ar); 9.09 (s, 1H, Ar). 13C NMR (DMSO-d6): δ 111.4, 112.6, 120.7, 121.8, 126.5, 127.2, 129.5, 138.2, 143.6, 144.3, 145.1, 147.2, 155.4.

출처