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Ethanol → 1-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

HRID 2106033
Notes
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Reaction equation

HRID 2106033 reaction equation
[OH:1][C:2]([C:31]([F:34])([F:33])[F:32])([CH2:15][C:16]([CH3:30])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2([CH3:29])OCC[O:25]2)[CH:19]=1)[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[C:24]([C:20]1[CH:19]=[C:18]([C:16]([CH3:30])([CH3:17])[CH2:15][C:2]([OH:1])([C:31]([F:32])([F:33])[F:34])[CH2:3][N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[CH:6]=[CH:5]2)[CH:23]=[CH:22][CH:21]=1)(=[O:25])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 22033616Pyridinium.p-toluenesulfonateHCID 578097811-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one

Product 1

HCID 578097551-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one (0.35 g, 0.75 mmol), ethanol (24 mL), water (4.8 mL), and pyridinium p-toluenesulfonic acid (95 mg, 0.37 mmol) was heated to reflux for 3 hours, cooled to room temperature, and concentrated in vacuo to remove most of the ethanol. The residue was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, and dried over sodium sulfate. Removal of the volatiles in vacuo afforded 1-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1-H-quinolin-4-one. Yield: 0.27 g (84%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. customto remove most of the ethanol
  5. additionThe residue was diluted with ethyl acetate and water
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-f1b3c0c15c60486e965bffd0e66bc88c
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07579469B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes