Water → 2,4-Dimethoxy-3-carbethoxyquinoline

HRID 73904

Reaktionsgleichung

Reaktionsgleichung von HRID 73904
[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-8e74050fae504d6886a5595d870485f1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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