Reaction #2069940

Reaction equation

1-bromo-4-butylbenzene

magnesium

sodium hydroxide

1-isoquinolinecarbonitrile

hydrochloric acid

1,2-dibromoethane

→

title compound

(4-butylphenyl)(1-isoquinolyl)ketone

Solvents

tetrahydrofuran

tetrahydrofuran

methanol

Conditions

Workup

1. 1
   Temperatureunder reflux for 10 minutes
2. 2
   workup.STIRRINGwas stirred for another 1 hour at room temperature
3. 3
   TemperatureSubsequently, the solution was cooled again to 0° C.
4. 4
   Temperaturerefluxed for 2 hours
5. 5
   Filtrationtoluene, and was filtered through celite
6. 6
   Washwashed with water
7. 7
   Dryingdried over magnesium sulfate
8. 8
   Concentrationconcentrated
9. 9
   OtherThe residue was purified by silica gel column chromatography

Procedure

Under a nitrogen atmosphere, 1-bromo-4-butylbenzene (2.29 ml, 13.0 mmol) was added to a mixed solution of magnesium (338 mg, 13.9 mmol) and tetrahydrofuran (6.5 ml), and as an initiator, catalytic amount of 1,2-dibromoethane was added, and this was stirred under reflux for 10 minutes. The solution was cooled to 0° C., a tetrahydrofuran solution of 1-isoquinolinecarbonitrile (1.0 g, 6.49 mmol) was added, and was stirred for another 1 hour at room temperature, and at 70° C. for 3 hours. Subsequently, the solution was cooled again to 0° C., concentrated hydrochloric acid (2.56 ml) and methanol (11 ml) were added, and then refluxed for 2 hours. The concentrated residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was divided, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.72 g of the title compound.

Source