Reaction #75426

Reaction equation

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 )

Yield 90.0%

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

Yield 90.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux under nitrogen for 17 hours
3. 3
   Temperaturethe mixture was refluxed for an additional 5 hours
4. 4
   OtherThe 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
   Washwas washed with brine
9. 9
   Dryingdried (MgSO4)
10. 10
    OtherThe solvent was removed under vacuum
11. 11
    Otherto leave an amber oil
12. 12
    OtherPurification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane)

Procedure

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