Sodium Hydroxide → 4-Chloro-6,7-dimethoxyquinoline

HRID 1375158Notes

Reaction equation

HRID 1375158 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[CH:13][CH2:12][C:11]2=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][C:11]1[C:10]2[C:15](=[CH:16][C:17]([O:18][CH3:19])=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 224782456,7-Dimethoxyquinolin-4(3H)-one

Product 1

HCID 4596104-Chloro-6,7-dimethoxyquinolineYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (3 L) and phosphorus oxychloride (1300 g) were added to 6,7-dimethoxy-4-quinolone (1056 g), and the mixture was heated under reflux with stirring for one hr. The reaction solution was neutralized with an aqueous sodium hydroxide solution at 0° C. The resultant precipitate was collected by filtration and was slurried in water (10 L) for washing. The slurry was filtered, and the filtered product was then dried under the reduced pressure to give 4-chloro-6,7-dimethoxyquinoline (928 g, yield 87.6%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationThe resultant precipitate was collected by filtration
  4. washfor washing
  5. filtrationThe slurry was filtered
  6. customthe filtered product was then dried under the reduced pressure

Sources & evidence

ORD record
ord-e9a9036c54a2409ca2a1b0f589baf7e9
Source dataset
uspto-grants-2007_01
Patent number
US07166722B2

Reaction notes

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