3-Hydroxybenzophenone → {3-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}phenylmethanone

HRID 228599

Reaction equation

HRID 228599 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.[OH:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][CH:30]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])O.[Na+]>>[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:16][C:17]1[CH:18]=[C:19]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 830503-HydroxybenzophenoneHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 53907205{3-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}phenylmethanoneYield 65.3%

Conditions

Temperature
170 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (112 mg) and 3-hydroxybenzophenone (297 mg) were mixed together, and the mixture was heated at 170° C. for 10 min. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane-acetone as a solvent to give the title compound (126 mg, yield 65%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over sodium sulfate
  4. concentrationwas then concentrated
  5. customThe residue was subjected to separation and purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-7f9cab0a07a442abbf9e7ddac8cc2348
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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