Реакция #75426

Уравнение реакции

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 )

Выход 90.0%

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

Выход 90.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux under nitrogen for 17 hours
3. 3
   Температураthe mixture was refluxed for an additional 5 hours
4. 4
   ДругоеThe solvent was removed under vacuum
5. 5
   workup.ADDITIONthe mixture was diluted with water
6. 6
   Экстракцияextracted twice with diethylether
7. 7
   ЭкстракцияThe organic extract
8. 8
   Промывкаwas washed with brine
9. 9
   Сушкаdried (MgSO4)
10. 10
    ДругоеThe solvent was removed under vacuum
11. 11
    Другоеto leave an amber oil
12. 12
    ДругоеPurification by flash chromatography (230-400 mesh silica gel; 10-25% ethyl acetate in hexane)

Методика

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).

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