Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinoline
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]=1Participants
3
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
- temperaturethe mixture was heated
- temperatureunder reflux for one hr
- customThe solvent was removed by distillation under the reduced pressure
- dissolutionThe residue was dissolved in chloroform
- additionby the addition of an aqueous sodium hydroxide solution
- extractionfollowed by extraction with chloroform
- dry with materialThe chloroform layer was dried over sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- customthe residue was purified by chromatography on silica gel by development with chloroform/acetone (10/1)
Sources & evidence
- ORD record
- ord-d7cc9b502af843a486b8309a61a228f9
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169789B2
Reaction notes
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