Sodium Iodide → 3-(3-Methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrile

HRID 1921330ノート

反応式

HRID 1921330 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19]C)=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[I-].[Na+].Cl[Si](C)(C)[CH3:25]>C(#N)C.O>[CH3:25][C:10]1[NH:11][C:12](=[O:19])[C:13]2[C:18]([C:9]=1[C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])=[CH:17][CH:16]=[CH:15][CH:14]=2

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 674925834-(3-Cyanophenyl)-1-methoxyisoquinoline

生成物 1

HCID 116945723-(3-Methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrile収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-(3-cyanophenyl)-1-methoxyisoquinoline (200 mg, 0.73 mmol) in acetonitrile (6 mL) is added sodium iodide (219 mg, 1.46 mmol) followed by chlorotrimethylsilane (186 μL, 1.46 mmol) and the mixture is heated at reflux for 1.5 hr. The cooled reaction is diluted with water (15 mL) and the solids are collected by filtration, washed with water and dried to give 3-(3-methyl-1-oxo-1,2-dihydroisoquinolin-4-yl)benzonitrile (157 mg, 83% yield). 1H NMR (δ ppm) 11.55 (1H, s), 8.22 (1H, d), 7.95 (1H, d), 7.82 (1H, s), 7.72 (1H, t), 7.66 (1H, m), 7.60 (1H, m), 7.47 (1H, t), 6.94 (1H, d), 1.99 (3H, s).

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1.5 hr
  3. customThe cooled reaction
  4. filtrationthe solids are collected by filtration
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-4fb519fc587f4eddbafb76a6c0d55d72
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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