Réaction #684960

Équation de réaction

potassium cyanide

benzoyl chloride

6,7-dimethoxyisoquinoline

→

title compound

Rendement 33.7%

2-Benzoyl-6,7-dimethoxy-1,2-dihydro-1-isoquinolinecarbonitrile

Rendement 33.7%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autrewas synthesized
2. 2
   Températurewhile heating
3. 3
   Températureunder reflux for 2 hours
4. 4
   Filtrationfiltered through celite
5. 5
   Lavagewashed with methylene chloride and water
6. 6
   AutreAfter the obtained filtrate was separated
7. 7
   Lavagethe methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    AutreThe residue was purified by silica gel column chromatography

Mode opératoire

An aqueous potassium cyanide (1.0 g, 16 mmol) solution (2.3 ml) and benzoyl chloride (1.1 ml, 9.5 mmol) were added to a solution of 6,7-dimethoxyisoquinoline (1.0 g, 5.3 mmol), which was synthesized according to Tetrahedron, 37 (23), 3977 (1981), in methylene chloride (6.0 ml), and this reaction mixture was stirred while heating under reflux for 2 hours. The reaction mixture was cooled to room temperature, filtered through celite, and washed with methylene chloride and water. After the obtained filtrate was separated, the methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide, 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 (573 mg).

Source