Reaction #684960

Reaction equation

potassium cyanide

benzoyl chloride

6,7-dimethoxyisoquinoline

→

title compound

Yield 33.7%

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

Yield 33.7%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherwas synthesized
2. 2
   Temperaturewhile heating
3. 3
   Temperatureunder reflux for 2 hours
4. 4
   Filtrationfiltered through celite
5. 5
   Washwashed with methylene chloride and water
6. 6
   OtherAfter the obtained filtrate was separated
7. 7
   Washthe methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    OtherThe residue was purified by silica gel column chromatography

Procedure

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