Ethanol → 5-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

HRID 2409773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409773
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.OS(O)(=O)=O.[CH3:29][CH2:30]O>>[CH2:29]([O:22][C:21]([C:18]1[CH:19]=[CH:20][C:11]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=2)=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:23])[CH3:30]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 592928765-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid

Produkt 1

HCID 592928505-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

Versuchsvorschrift

A mixture of 5-(3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.2) (2 g), H2SO4 conc. (0.6 mL) and EtOH (100 mL) was stirred at reflux for 30 h, allowed to cool and concentrated. The residue was diluted in EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 1.77 g of the title compound as a white solid. Title compound: ESI-MS: 338.2 [M+H]+; tR 3.81 min (System 1); TLC: Rf=0.29 (Hex/EtOAc, 3:2).

Aufarbeitung

  1. temperatureat reflux for 30 h
  2. temperatureto cool
  3. concentrationconcentrated
  4. additionThe residue was diluted in EtOAc
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with H2O and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-070f7d1b826b49f29e24dbfcf6d737f6
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815901B2

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