反应 #607455

反应方程式

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

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

溶剂

pyridine

NaOH

反应条件

后处理

1. 1
   其他to quench
2. 2
   其他the reaction
3. 3
   其他the solvent was evaporated under reduced pressure
4. 4
   其他to afford an orange solid
5. 5
   温度After cooling on ice the pH
6. 6
   其他The solid that precipitated
7. 7
   过滤was filtered off
8. 8
   洗涤washed with water and ether
9. 9
   萃取Then extracted with ethyl acetate (3 times 15 ml)
10. 10
    洗涤washed with water (3 time 15 ml)
11. 11
    干燥dried over MgSO4
12. 12
    其他The solvent was evaporated
13. 13
    其他the residue was dried

实验过程

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.

来源