Réaction #75426

Équation de réaction

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 )

Rendement 90.0%

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

Rendement 90.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux under nitrogen for 17 hours
3. 3
   Températurethe mixture was refluxed for an additional 5 hours
4. 4
   AutreThe solvent was removed under vacuum
5. 5
   workup.ADDITIONthe mixture was diluted with water
6. 6
   Extractionextracted twice with diethylether
7. 7
   ExtractionThe organic extract
8. 8
   Lavagewas washed with brine
9. 9
   Séchagedried (MgSO4)
10. 10
    AutreThe solvent was removed under vacuum
11. 11
    Autreto leave an amber oil
12. 12
    AutrePurification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane)

Mode opératoire

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).

Source