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

HRID 1921330노트

반응식

HRID 1921330 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4fb519fc587f4eddbafb76a6c0d55d72
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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