Water → 2,4-Dimethoxy-3-carbethoxyquinoline

HRID 423731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423731
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[Li]CCCC.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].O>C1COCC1>[CH3:1][O:2][C:3]1[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:11]([O:13][CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 1424362,4-DimethoxyquinolineHCID 178418339Butyllithium

Produkt 1

HCID 129326352,4-Dimethoxy-3-carbethoxyquinolineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2,4-dimethoxyquinoline (11.5 g, 60.8 mmol) in anhydrous THF was added dropwise n-BuLi (2.5 M in hexane, 48.6 mL, 122 mmol) at 0° C. After stirring for 1.5 h at 0° C., the mixture was added to a solution of ethyl chloroformate in anhydrous THF and stirred at 0° C. for additional 30 min and then at room temperature overnight. The reaction mixture was poured into water and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under vacuum. The resulting residue was purified by column chromatography (petroleum ether/EtOAc=50/1) to give ethyl 2,4-dimethoxyquinoline-3-carboxylate (9.6 g, 60%).

Aufarbeitung

  1. stirringstirred at 0° C. for additional 30 min
  2. customat room temperature
  3. customovernight
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography (petroleum ether/EtOAc=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-3064ff7f53204c50b45b28725fd0f52c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101767B2

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