Реакция #684960

Уравнение реакции

potassium cyanide

benzoyl chloride

6,7-dimethoxyisoquinoline

→

title compound

Выход 33.7%

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

Выход 33.7%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Другоеwas synthesized
2. 2
   Температураwhile heating
3. 3
   Температураunder reflux for 2 hours
4. 4
   Фильтрацияfiltered through celite
5. 5
   Промывкаwashed with methylene chloride and water
6. 6
   ДругоеAfter the obtained filtrate was separated
7. 7
   Промывкаthe methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide
8. 8
   Сушкаdried over anhydrous magnesium sulfate
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеThe residue was purified by silica gel column chromatography

Методика

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).

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