Reacción #75426

Ecuación de reacción

1-Iodopropane

(R)-5-Propylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

1-iodopropane

potassium carbonate

→

title compound ( 9b )

Rendimiento 90.0%

(R)-5-Dipropylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Rendimiento 90.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux under nitrogen for 17 hours
3. 3
   Temperaturathe mixture was refluxed for an additional 5 hours
4. 4
   OtroThe solvent was removed under vacuum
5. 5
   workup.ADDITIONthe mixture was diluted with water
6. 6
   Extracciónextracted twice with diethylether
7. 7
   ExtracciónThe organic extract
8. 8
   Lavadowas washed with brine
9. 9
   Secadodried (MgSO4)
10. 10
    OtroThe solvent was removed under vacuum
11. 11
    Otroto leave an amber oil
12. 12
    OtroPurification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane)

Procedimiento

Following the procedure of Example 3, a mixture of (R)-5-Propylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (8b, 0.93 g, 3.56 mmol) 1-iodopropane (3.05 g, 17.9 mmol), and potassium carbonate (1.97 g, 14.3 mmol) in acetonitrile (25 ml) was heated at reflux under nitrogen for 17 hours. 1-Iodopropane (3.05 g, 17.9 mmol) was again added, and the mixture was refluxed for an additional 5 hours. The solvent was removed under vacuum, and the mixture was diluted with water and extracted twice with diethylether. The organic extract was washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an amber oil. Purification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane) gave the title compound (9b) as an amber oil (0.87 g, 90% yield).

Fuente