Benzoyl chloride → 2-Benzoyl-6,7-dimethoxy-1,2-dihydroisoquinoline-1-carbonitrile

HRID 597778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597778
[C-:1]#[N:2].[K+].[C:4](Cl)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[CH:21]=[N:20][CH:19]=[CH:18]2>C(Cl)Cl>[C:4]([N:20]1[CH:19]=[CH:18][C:17]2[C:22](=[CH:23][C:24]([O:25][CH3:26])=[C:15]([O:14][CH3:13])[CH:16]=2)[CH:21]1[C:1]#[N:2])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 1775786,7-Dimethoxyisoquinoline

Produkt 1

HCID 3147402-Benzoyl-6,7-dimethoxy-1,2-dihydroisoquinoline-1-carbonitrileAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customwas synthesized
  2. temperaturewhile heating
  3. temperatureunder reflux for 2 hours
  4. filtrationfiltered through celite
  5. washwashed with methylene chloride and water
  6. customAfter the obtained filtrate was separated
  7. washthe methylene chloride layer was washed successively with water, 2 N hydrochloric acid, water, and 2 N sodium hydroxide
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-27ebd9a538bd4858ac865e40bb3c84a4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897387B2

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