1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → HCID 24879270, compound

HRID 228701Notes

Reaction equation

HRID 228701 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])=[O:3].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:26][CH3:27])[N:17]=[CH:16][CH:15]=[C:14]2[O:12][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 24879270HCID 24879270, compoundYield 10.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

2-Hydroxy-5-methoxyacetophenone (11.1 g), 4-chloro-6,7-dimethoxyquinoline (5.00 g), and 4-dimethylaminopyridine (8.10 g) were suspended in o-dichlorobenzene (40 ml) to prepare a suspension which was then stirred at 120° C. for 48 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give 1-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methoxy-phenyl]-ethanone (802 mg, yield 10%).

Workup

  1. customto prepare a suspension which
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was then washed with water and saturated brine
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3db23b8951644ee4a04505d755581f60
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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