Potassium Carbonate → 4-Hydroxyquinoline

HRID 2106034

Reaktionsgleichung

Reaktionsgleichung von HRID 2106034
C(C1C=C(C(C)(C)CC(O)(C(F)(F)F)C[N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[CH:16]=[CH:15]2)C=CC=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl.NO>CO>[NH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[CH:16]=[CH:15]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 578097551-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Produkt 1

HCID 691414-Hydroxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 1-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1-H-quinolin-4-one (60 mg, 0.14 mmol), potassium carbonate (79 mg, 0.57 mmol), and hydroxylamine hydrochloride (39 mg, 0.55 mmol) in methanol (1 mL) was heated at 65° C. for 3 hours, cooled to room temperature, and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography to afford 1-(2-hydroxy-4-{3-[1-(hydroxyimino)ethyl]phenyl)}-4-methyl-2-trifluoromethylpentyl)-1H-quinolin-4-one. Yield: 38 mg.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-62aed791fe1f4c198a3cee629f07deca
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

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