Reacción #2069953

Ecuación de reacción

potassium cyanide

benzoyl chloride

6,7-dimethoxyisoquinoline

→

title compound

Rendimiento 33.7%

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

Rendimiento 33.7%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas synthesized
2. 2
   Temperaturawhile heating
3. 3
   Temperaturaunder reflux for 2 hours
4. 4
   Filtraciónfiltered through celite
5. 5
   Lavadowashed with methylene chloride and water
6. 6
   OtroAfter the obtained filtrate was separated
7. 7
   Lavadothe methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroThe residue was purified by silica gel column chromatography

Procedimiento

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).

Fuente