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

HRID 604785ノート

反応式

HRID 604785 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5e34a7df75e34a85a586a76a6559af7e
出典データセット
uspto-grants-2011_03
特許番号
US07910712B2

反応ノート

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