Phosphorus oxychloride → HCID 10084233, compound

HRID 1382277Notes

Reaction equation

HRID 1382277 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5].P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:15]1[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4](=[O:5])[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11776709HCID 11776709, compound

Product 1

HCID 10084233HCID 10084233, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Methoxyacetyl-8-methoxy-4-(1H)-quinolone (39 g, 0.16 mol) was heated under reflux in a mixture of phosphoryl chloride (150 ml) and chloroform (200 ml) for 45 minutes. The solvent was evaporated and the mixture was partitioned between chloroform and sodium hydrogen carbonate solution. The aqueous layer was separated and extracted with chloroform. The combined organic solutions were washed with sodium hydrogen carbonate solution and brine. Evaporation gave an oil which afforded yellow crystals of 4-chloro-8-methoxy-3-methoxyacetylquinoline (19.2 g, 45.8%), m.p. 96°-8°.

Workup

  1. customThe solvent was evaporated
  2. customthe mixture was partitioned between chloroform and sodium hydrogen carbonate solution
  3. customThe aqueous layer was separated
  4. extractionextracted with chloroform
  5. washThe combined organic solutions were washed with sodium hydrogen carbonate solution and brine
  6. customEvaporation
  7. customgave an oil which

Sources & evidence

ORD record
ord-00152ddeb2f648a598674d370bce7fe3
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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