تفاعل #607455

معادلة التفاعل

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

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

المذيبات

pyridine

NaOH

ظروف التفاعل

المعالجة

1. 1
   أخرىto quench
2. 2
   أخرىthe reaction
3. 3
   أخرىthe solvent was evaporated under reduced pressure
4. 4
   أخرىto afford an orange solid
5. 5
   درجة الحرارةAfter cooling on ice the pH
6. 6
   أخرىThe solid that precipitated
7. 7
   ترشيحwas filtered off
8. 8
   غسيلwashed with water and ether
9. 9
   استخلاصThen extracted with ethyl acetate (3 times 15 ml)
10. 10
    غسيلwashed with water (3 time 15 ml)
11. 11
    تجفيفdried over MgSO4
12. 12
    أخرىThe solvent was evaporated
13. 13
    أخرىthe residue was dried

الإجراء التجريبي

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.

المصدر