Reacción #607455

Ecuación de reacción

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

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

Disolventes

pyridine

NaOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench
2. 2
   Otrothe reaction
3. 3
   Otrothe solvent was evaporated under reduced pressure
4. 4
   Otroto afford an orange solid
5. 5
   TemperaturaAfter cooling on ice the pH
6. 6
   OtroThe solid that precipitated
7. 7
   Filtraciónwas filtered off
8. 8
   Lavadowashed with water and ether
9. 9
   ExtracciónThen extracted with ethyl acetate (3 times 15 ml)
10. 10
    Lavadowashed with water (3 time 15 ml)
11. 11
    Secadodried over MgSO4
12. 12
    OtroThe solvent was evaporated
13. 13
    Otrothe residue was dried

Procedimiento

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.

Fuente