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

HRID 1673087Notes

Reaction equation

HRID 1673087 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 3147402-Benzoyl-6,7-dimethoxy-1,2-dihydroisoquinoline-1-carbonitrileYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  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

Sources & evidence

ORD record
ord-a2e4ef1b92f94c3a904cc85e35603754
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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