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Water → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-2-ethyl-[1,6]naphthyridine

HRID 229041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 229041
[CH2:1]([C:3]1[C:12]([OH:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[N:4]=1)[CH3:2].Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][CH:16]=[C:15]2[O:13][C:12]1[C:3]([CH2:1][CH3:2])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][N:8]=[CH:7][CH:6]=2
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Komponenten

6

Edukt 3

HCID 962WaterHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 230783992-Ethyl-[1,6]naphthyridin-3-ol

Produkt 1

HCID 230782643-(6,7-Dimethoxy-quinolin-4-yloxy)-2-ethyl-[1,6]naphthyridineAusbeute 6,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 7239
1,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

2-Ethyl-[1,6]naphthyridin-3-ol (69 mg), 4-chloro-6,7-dimethoxyquinoline (265 mg), and 4-dimethylaminopyridine (145 mg) were suspended in o-dichlorobenzene (3 ml), and the mixture was stirred at 140° C. for 4 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (9 mg, yield 6%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c7f51bdfad264d189094e4aaa0aa4396
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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