2-Hydroxy-4-methoxy-4'-methylbenzophenone → HCID 57756379, compound

HRID 228586Notes

Reaction equation

HRID 228586 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:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)=[O:20]>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:16][C:17]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:18]=1[C:19]([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:20]

Participants

5

Reactant 2

HCID 716452-Hydroxy-4-methoxy-4'-methylbenzophenoneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 57756379HCID 57756379, compoundYield 43%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (56 mg), 2-hydroxy-4-methoxy-4′-methylbenzophenone (242 mg), and 4-dimethylaminopyridine (122 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 4 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-hexane to give the title compound (46 mg, yield 43%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  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 thin layer chromatography

Sources & evidence

ORD record
ord-6ca39c94394d4d74b447496787b6f49b
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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