Реакция #607455

Уравнение реакции

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

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

Растворители

pyridine

NaOH

Условия реакции

Обработка

1. 1
   Другоеto quench
2. 2
   Другоеthe reaction
3. 3
   Другоеthe solvent was evaporated under reduced pressure
4. 4
   Другоеto afford an orange solid
5. 5
   ТемператураAfter cooling on ice the pH
6. 6
   ДругоеThe solid that precipitated
7. 7
   Фильтрацияwas filtered off
8. 8
   Промывкаwashed with water and ether
9. 9
   ЭкстракцияThen extracted with ethyl acetate (3 times 15 ml)
10. 10
    Промывкаwashed with water (3 time 15 ml)
11. 11
    Сушкаdried over MgSO4
12. 12
    ДругоеThe solvent was evaporated
13. 13
    Другоеthe residue was dried

Методика

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.

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