Methanol → 4-Methoxyquinoline

HRID 39728

Reaktionsgleichung

Reaktionsgleichung von HRID 39728
CO.[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[CH:14](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C.CCCCCC>C(#N)C>[CH3:14][O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 86587183Trimethylsilyldiazomethane hexaneHCID 178516385quinolin-4-ol

Produkt 1

HCID 5219384-Methoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 15 mL of methanol containing 4.02 g of 4-hydroxyquinoline and 130 mL of an acetonitrile solution, 5.01 g of diisopropylethylamine and 19.4 mL of a 2.0 mol/L trimethylsilyldiazomethane/hexane solution were added at room temperature, and the mixture was stirred for 13 hours, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate 2:1] to obtain 1.79 g of a yellow oily substance, 4-methoxyquinoline.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate 2:1]

Quellen und Nachweise

ORD-Eintrag
ord-02d91b4db9784466a5b7377a1c928c93
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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