Réaction #684954

Équation de réaction

sodium hydroxide

1-isoquinolinecarbonitrile

hydrochloric acid

4-Bromoanisol

1,2-dibromoethane

magnesium

→

title compound

1-Isoquinolyl(4-methoxyphenyl)ketone

Solvants

tetrahydrofuran

methanol

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurewhile heating
2. 2
   Températureunder 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
   Températurethis mixture was heated
6. 6
   Températureunder reflux for 1.5 hours
7. 7
   TempératureAfter cooling on ice
8. 8
   Extractionextracted with ether
9. 9
   Lavagewashed with saturated brine
10. 10
    Séchagedried over anhydrous magnesium sulfate
11. 11
    Concentrationconcentrated under reduced pressure
12. 12
    AutreThe residue was purified by silica gel column chromatography

Mode opératoire

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).

Source