反応 #684949

反応方程式

hydrochloric acid

1-Bromo-4-butylbenzene

1,2-dibromoethane

magnesium

tetrahydrofuran

1-isoquinolinecarbonitrile

tetrahydrofuran

→

title compound

(4-Butylphenyl)(1-isoquinolyl)ketone

溶媒

methanol

反応条件

後処理

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
   濃縮After the mixture was concentrated
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 5 N sodium hydroxide
8. 8
   ろ過toluene, and was filtered through celite
9. 9
   その他The toluene layer of the filtrate was separated
10. 10
    洗浄washed with water
11. 11
    乾燥dried over anhydrous magnesium sulfate
12. 12
    濃縮concentrated under reduced pressure
13. 13
    その他The residue was purified by silica gel column chromatography

実験手順

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).

出典