2-Acetyl-4-fluorophenol → HCID 24879101, compound

HRID 228542

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][C:17]([C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26])=[O:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[C:17](=[O:18])[CH3:16]

Participants

Conditions

Temperature: 160 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (58.2 mg), 5-fluoro-2-hydroxyacetophenone (409 mg), and 4-dimethylaminopyridine (317 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 8 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Chloroform was added to the residue, and the organic layer was washed with a 1 N aqueous potassium hydroxide solution and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform and by thin layer chromatography using acetone-hexane to give the title compound (63.5 mg, yield 72%).

Workup

temperatureThe reaction solution was cooled to room temperature
customthe solvent was then removed
distillationby distillation under the reduced pressure
additionChloroform was added to the residue
washthe organic layer was washed with a 1 N aqueous potassium hydroxide solution and saturated brine
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed
distillationby distillation under the reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-292ee15e054a4432bd8fe045a6d76269
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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