반응 #684949

반응 방정식

hydrochloric acid

1-Bromo-4-butylbenzene

1,2-dibromoethane

magnesium

tetrahydrofuran

1-isoquinolinecarbonitrile

tetrahydrofuran

→

title compound

(4-Butylphenyl)(1-isoquinolyl)ketone

용매

methanol

반응 조건

후처리

1. 1
   온도under reflux for 10 minutes
2. 2
   workup.STIRRINGthis mixture was stirred at room temperature for 1 hour
3. 3
   온도Thereafter, the mixture was cooled again to 0° C.
4. 4
   온도this mixture was heated
5. 5
   온도under reflux for 2 hours
6. 6
   농축After the mixture was concentrated
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 5 N sodium hydroxide
8. 8
   여과toluene, and was filtered through celite
9. 9
   기타The toluene layer of the filtrate was separated
10. 10
    세척washed with water
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    농축concentrated under reduced pressure
13. 13
    기타The residue was purified by silica gel column chromatography

실험 절차

1-Bromo-4-butylbenzene (2.29 ml, 13 mmol) and a catalytic amount of 1,2-dibromoethane as an initiator were added to a mixed solution of magnesium (338 mg, 14 mmol) and tetrahydrofuran (6.5 ml) under nitrogen atmosphere, and this mixture was stirred under reflux for 10 minutes. The mixture was cooled to 0° C., a solution of 1-isoquinolinecarbonitrile (1.0 g, 6.5 mmol) in tetrahydrofuran was added, and this mixture was stirred at room temperature for 1 hour, then at 70° C. for 3 hours. Thereafter, the mixture was cooled again to 0° C., concentrated hydrochloric acid (2.6 ml) and methanol (11 ml) were added, and this mixture was heated under reflux for 2 hours. After the mixture was concentrated, the residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was separated, washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.7 g).

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