Réaction #684949

Équation de réaction

hydrochloric acid

1-Bromo-4-butylbenzene

1,2-dibromoethane

magnesium

tetrahydrofuran

1-isoquinolinecarbonitrile

tetrahydrofuran

→

title compound

(4-Butylphenyl)(1-isoquinolyl)ketone

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 10 minutes
2. 2
   workup.STIRRINGthis mixture was stirred at room temperature for 1 hour
3. 3
   TempératureThereafter, the mixture was cooled again to 0° C.
4. 4
   Températurethis mixture was heated
5. 5
   Températureunder reflux for 2 hours
6. 6
   ConcentrationAfter the mixture was concentrated
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 5 N sodium hydroxide
8. 8
   Filtrationtoluene, and was filtered through celite
9. 9
   AutreThe toluene layer of the filtrate was separated
10. 10
    Lavagewashed with water
11. 11
    Séchagedried over anhydrous magnesium sulfate
12. 12
    Concentrationconcentrated under reduced pressure
13. 13
    AutreThe residue was purified by silica gel column chromatography

Mode opératoire

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).

Source