Reacción #2069947

Ecuación de reacción

sodium hydroxide

1-isoquinolinecarbonitrile

hydrochloric acid

4-Bromoanisol

1,2-dibromoethane

magnesium

→

title compound

1-Isoquinolyl(4-methoxyphenyl)ketone

Disolventes

tetrahydrofuran

methanol

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile heating
2. 2
   Temperaturaunder reflux for 45 minutes
3. 3
   workup.STIRRINGthis reaction mixture was stirred at room temperature for 2 hours
4. 4
   workup.ADDITIONwere added
5. 5
   Temperaturathis mixture was heated
6. 6
   Temperaturaunder reflux for 1.5 hours
7. 7
   TemperaturaAfter cooling on ice
8. 8
   Extracciónextracted with ether
9. 9
   Lavadowashed with saturated brine
10. 10
    Secadodried over anhydrous magnesium sulfate
11. 11
    Concentraciónconcentrated under reduced pressure
12. 12
    OtroThe residue was purified by silica gel column chromatography

Procedimiento

4-Bromoanisol (15.3 ml, 122 mmol) and a catalytic amount of 1,2-dibromoethane as an initiator were added to a mixed solution of magnesium (3059 mg, 125.8 mmol) and tetrahydrofuran (20 ml) under nitrogen atmosphere, and this reaction mixture was stirred while heating under reflux for 45 minutes. The mixture was cooled to 0° C., a solution of 1-isoquinolinecarbonitrile (10.78 g, 69.9 mmol) in tetrahydrofuran (30 ml) was added dropwise thereto, and this reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled on ice, concentrated hydrochloric acid (24 ml) and methanol (120 ml) were added, and this mixture was heated under reflux for 1.5 hours. After cooling on ice, the mixture was adjusted to pH 8 by adding aqueous sodium hydroxide, extracted with ether, washed with saturated brine, 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 (15.87 g).

Fuente