Phosphorus oxychloride → 2-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

HRID 375249

Reaction equation

HRID 375249 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([F:16])=[C:11]([F:17])[CH:10]=2)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:21])=O>O>[Cl:21][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([F:17])=[C:12]([F:16])[CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 199573073-Ethoxycarbonyl-6,7-difluorocarbostyril

Product 1

HCID 97954612-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

50 g of 3-ethoxycarbonyl-6,7-difluorocarbostyril are added in the course of 10 minutes with stirring at 20° C. to 200 cm3 of phosphoryl chloride. The suspension is heated to a temperature in the region of 70° C. and maintained at this temperature for 3 hours. After cooling to approximately 10° C., the solution obtained is poured with stirring into a mixture of 1,000 cm3 of water and 1,000 g of crushed ice. The temperature is allowed to rise to approximately 20° C. and the mixture is extracted with twice 500 cm3 of dichloromethane. The combined organic extracts are washed with 1,000 cm3 of water, and 1,000 cm3 of water to which sodium bicarbonate has been added to pH 7, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure (20 kPa) at approximately 40° C. 45.6 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline are obtained in the form of a beige solid, melting point 108° C. which is used without further purification for the subsequent steps.

Workup

  1. temperaturemaintained at this temperature for 3 hours
  2. temperatureAfter cooling to approximately 10° C.
  3. customthe solution obtained
  4. additionis poured
  5. customto rise to approximately 20° C.
  6. extractionthe mixture is extracted with twice 500 cm3 of dichloromethane
  7. washThe combined organic extracts are washed with 1,000 cm3 of water, and 1,000 cm3 of water to which sodium bicarbonate
  8. additionhas been added to pH 7
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 kPa) at approximately 40° C

Sources & evidence

ORD record
ord-be6f8b6a30fb44e59153efa24c1cdea9
Source dataset
uspto-grants-1996_01
Patent number
US05484921

Linked notes

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