Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinoline

HRID 1008323Notes

Reaction equation

HRID 1008323 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](=O)[CH:19]=[CH:20][NH:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([Cl:3])=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:25][CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-ol

Product 1

HCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinolineYield 21%

Procedure

Phosphorus oxychloride (14.19 ml) was added to 7-(benzyloxy)-6-methoxy-1,4-dihydro-4-quinolinone (17.16 g), and the mixture was heated under reflux for one hr. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in chloroform, and the solution was made alkaline by the addition of an aqueous sodium hydroxide solution, followed by extraction with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by chromatography on silica gel by development with chloroform/acetone (10/1) to give 3.82 g (yield 21%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hr
  3. customThe solvent was removed by distillation under the reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. additionby the addition of an aqueous sodium hydroxide solution
  6. extractionfollowed by extraction with chloroform
  7. dry with materialThe chloroform layer was dried over sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by chromatography on silica gel by development with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-78d38b0edb834cb798b43783dc3d3475
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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