反応 #75426

反応方程式

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 )

収率 90.0%

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

収率 90.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux under nitrogen for 17 hours
3. 3
   温度the mixture was refluxed for an additional 5 hours
4. 4
   その他The solvent was removed under vacuum
5. 5
   workup.ADDITIONthe mixture was diluted with water
6. 6
   抽出extracted twice with diethylether
7. 7
   抽出The organic extract
8. 8
   洗浄was washed with brine
9. 9
   乾燥dried (MgSO4)
10. 10
    その他The solvent was removed under vacuum
11. 11
    その他to leave an amber oil
12. 12
    その他Purification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane)

実験手順

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).

出典