Reaktion #1027

Reaktionsgleichung

Methyl magnesium chloride

isoquinoline-3-carbonitrile

THF

→

3-acetyl-isoquinoline

Ausbeute 14.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   Sonstigequenched with water
3. 3
   workup.ADDITIONHydrochloric acid (2M aqueous solution) was added to the reaction mixture until the aqueous phase
4. 4
   workup.STIRRINGAfter stirring for 30 minutes the
5. 5
   Extraktionextracted with ether (×2)
6. 6
   WaschenThe combined extracts were washed with water
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give a crystalline solid
10. 10
    SonstigeRecrystalisation from hexane

Vorschrift

Methyl magnesium chloride (2.6 ml of a 3.0M solution in THF) was added dropwise to a solution of isoquinoline-3-carbonitrile at 0°-5° C. After the addition the reaction mixture was stirred at room temperature for 1 hour, then quenched with water. Hydrochloric acid (2M aqueous solution) was added to the reaction mixture until the aqueous phase was pH2. After stirring for 30 minutes the aqueous was neutralised with sodium bicarbonate (solid) and extracted with ether (×2). The combined extracts were washed with water, dried and concentrated to give a crystalline solid. Recrystalisation from hexane gave 3-acetyl-isoquinoline (0.55 g, 14% yield) as a pale yellow solid m.p. 84.4°-86.8° C. 1H NMR: 2.83(3H,s); 7.69-7.81(2H,m); 7.99(1H,m); 8.04(1H,m); 8.49(1H,m); 9.29(1H,s) ppm.

Quelle