Potassium Carbonate → 4-Hydroxyquinoline

HRID 2106034

Reaction equation

HRID 2106034 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 691414-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-62aed791fe1f4c198a3cee629f07deca
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Linked notes

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