反应 #684949

反应方程式

hydrochloric acid

1-Bromo-4-butylbenzene

1,2-dibromoethane

magnesium

tetrahydrofuran

1-isoquinolinecarbonitrile

tetrahydrofuran

→

title compound

(4-Butylphenyl)(1-isoquinolyl)ketone

溶剂

methanol

反应条件

后处理

1. 1
   温度under reflux for 10 minutes
2. 2
   workup.STIRRINGthis mixture was stirred at room temperature for 1 hour
3. 3
   温度Thereafter, the mixture was cooled again to 0° C.
4. 4
   温度this mixture was heated
5. 5
   温度under reflux for 2 hours
6. 6
   浓缩After the mixture was concentrated
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 5 N sodium hydroxide
8. 8
   过滤toluene, and was filtered through celite
9. 9
   其他The toluene layer of the filtrate was separated
10. 10
    洗涤washed with water
11. 11
    干燥dried over anhydrous magnesium sulfate
12. 12
    浓缩concentrated under reduced pressure
13. 13
    其他The residue was purified by silica gel column chromatography

实验过程

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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