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

HRID 1921330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921330
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fb519fc587f4eddbafb76a6c0d55d72
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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