تفاعل #684954

معادلة التفاعل

sodium hydroxide

1-isoquinolinecarbonitrile

hydrochloric acid

4-Bromoanisol

1,2-dibromoethane

magnesium

→

title compound

1-Isoquinolyl(4-methoxyphenyl)ketone

المذيبات

tetrahydrofuran

methanol

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile heating
2. 2
   درجة الحرارةunder 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
   درجة الحرارةthis mixture was heated
6. 6
   درجة الحرارةunder reflux for 1.5 hours
7. 7
   درجة الحرارةAfter cooling on ice
8. 8
   استخلاصextracted with ether
9. 9
   غسيلwashed with saturated brine
10. 10
    تجفيفdried over anhydrous magnesium sulfate
11. 11
    تركيزconcentrated under reduced pressure
12. 12
    أخرىThe residue was purified by silica gel column chromatography

الإجراء التجريبي

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).

المصدر