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2-Iodo-6-methylpyridin-3-ol → 7-Benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinoline

HRID 228926
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228926
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH2:24]([O:23][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([O:8][C:7]3[C:2]([I:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=3)=[CH:12][CH:13]=[N:14]2)=[CH:19][C:18]=1[O:21][CH3:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 899572-Iodo-6-methylpyridin-3-olHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Produkt 1

HCID 230783237-Benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxyquinolineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 72391,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

2-Iodo-6-picolin-3-ol (10 g), 4-chloro-7-benzyloxy-6-methoxyquinoline (6.8 g), and 4-(N,N-dimethylamino)-pyridine (12.2 g) were dissolved in 1,2-dichlorobenzene (400 ml) to prepare a solution, and the mixture was stirred at 125° C. overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, the mixture was extracted with chloroform, and the chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using chloroform-acetone to give 7-benzyloxy-4-(2-iodo-6-methyl-pyridin-3-yloxy)-6-methoxy-quinoline (5.2 g, yield 31%).

Aufarbeitung

  1. customto prepare a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washthe chloroform layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7827b17d3f3644edb1816e665f69888b
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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