5'-Bromo-2'-hydroxyacetophenone → HCID 57756584, compound

HRID 228543Notes

Reaction equation

HRID 228543 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]([Br:25])[CH:22]=[CH:21][C:20]=1[OH:26])=[O:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Br:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[C:19]([C:17](=[O:18])[CH3:16])[CH:24]=1

Participants

5

Reactant 2

HCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 57756584HCID 57756584, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (113 mg), 5-bromo-2-hydroxyacetophenone (550 mg), and 4-dimethylaminopyridine (311 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 4 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 (96.2 mg, yield 47%).

Workup

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

Sources & evidence

ORD record
ord-abef4c78cf1e45eea0a502feba21c158
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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