Phosphorus oxychloride → HCID 10377394, compound

HRID 1647487Notes

Reaction equation

HRID 1647487 reaction equation
[C:1]([C:5]1[C:14](=O)[C:13]2[C:8](=[C:9]([O:16][CH3:17])[CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].P(Cl)(Cl)([Cl:20])=O>>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:20])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH3:17])(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10036866HCID 10036866, compound

Product 1

HCID 10377394HCID 10377394, compound

Procedure

3-Propanoyl-8-methoxy-4(1H)-quinolone (35.4 g, 0.15 mol) was dissolved in phosphoryl chloride (400 ml) and heated at reflux for 1 hour, then the excess phosphoryl chloride evaporated. The residue was mixed with ice, then diluted with water and extracted into dichloromethane. Drying and evaporation gave 3-propanoyl-4-chloro-8-methoxyquinoline (39.7 g) as a dark oil which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customthe excess phosphoryl chloride evaporated
  4. additionThe residue was mixed with ice
  5. additiondiluted with water
  6. extractionextracted into dichloromethane
  7. customDrying
  8. customevaporation

Sources & evidence

ORD record
ord-3ad91f5d8fea473e9f4e3f9b0ea3da2c
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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