Sodium Hydroxide → {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-(phenyl)methanone hydrochloride

HRID 228592

Reaction equation

HRID 228592 reaction equation
[Cl:1][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:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].[OH-].[Na+]>C(Cl)(Cl)Cl>[ClH:1].[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:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=1[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 738512-Hydroxy-5-methylbenzophenoneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 24879060{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-(phenyl)methanone hydrochlorideYield 12%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Chloro-6,7-dimethoxyquinoline (1.00 g) and 2-hydroxy-5-methylbenzophenone (1.14 g) were stirred at 170° C. for one hr. The reaction solution was cooled to room temperature. Chloroform was then added to the reaction solution, and separation was carried out with a 10% aqueous sodium hydroxide solution. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel using hexane-acetone. Thereafter, 10% hydrochloric acid-methanol (10 ml) was added to the product, followed by concentration. The concentrate was suspended in ether, and the suspension was filtered to give the title compound (234 mg, yield 12%).

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. customThe solvent was removed
  4. distillationby distillation under the reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. additionThereafter, 10% hydrochloric acid-methanol (10 ml) was added to the product
  7. concentrationfollowed by concentration
  8. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-d9fec07b4a73464c9efe7ffbfcbddea2
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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