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Potassium Iodide → Acetonitrile, [(5,7-dichloro-2-methyl-8-quinolinyl)oxy]-

HRID 1731894
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1731894
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:24][C:25]#[N:26]>CC(=O)CC.O>[CH3:14][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[C:9]([O:13][CH2:24][C:25]#[N:26])[C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 6301ChlorquinaldolHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Produkt 1

HCID 2681672Acetonitrile, [(5,7-dichloro-2-methyl-8-quinolinyl)oxy]-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 6569Methyl Ethyl KetoneLösungsmittel2×

Versuchsvorschrift

10.7 g of 5,7-dichloro-8-hydroxyquinaldine are dissolved at elevated temperature in 150 ml of 2-butanone; 10.4 g of potassium carbonate are then added portionwise, and the mixture is refluxed for one hour. After the addition of 1 g of potassium iodide, there are added dropwise, with stirring and refluxing, 7.1 g of chloroacetonitrile in 30 ml of 2-butanone, and the mixture is subsequently heated for 3 hours at an internal temperature of 75° C. To the resulting reaction mixture, after cooling to room temperature, is added 1 liter of water, and the whole is filtered; the residue is washed with water, dried, and recrystallised from chloroform/petroleum ether (40°-60° C.) to thus obtain 2-methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline, m.p. 157°-158° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed for one hour
  2. additionare added dropwise
  3. temperaturerefluxing
  4. customTo the resulting reaction mixture
  5. filtrationthe whole is filtered
  6. washthe residue is washed with water
  7. customdried
  8. customrecrystallised from chloroform/petroleum ether (40°-60° C.) to thus obtain 2-methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline, m.p. 157°-158° C.

Quellen und Nachweise

ORD-Eintrag
ord-1d138d56a3844ce2b0ca4627b6a3d246
Quelldatensatz
uspto-grants-1986_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04623727

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