Phosphorus oxychloride → 3-Butyryl-4-chloro-8-methoxyquinoline

HRID 1382259Notes

Reaction equation

HRID 1382259 reaction equation
[C:1]([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])[CH2:2][CH2:3][CH3:4].C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:26])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:26])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 103321024(1H)-Quinolinone, 8-methoxy-3-(1-oxobutyl)-

Product 1

HCID 117775673-Butyryl-4-chloro-8-methoxyquinolineYield 58.5%

Procedure

3-Butyryl-8-methoxy-4(1H)-quinolone (9.0 g, 0.037 mol) and phosphorus oxychloride (100 ml) were heated under reflux for 30 minutes. When cool, the mixture was poured onto ice, adjusted to pH 4 with sodium bicarbonate and extracted with dichloromethane. Evaporation and crystallisation from ethyl acetate-petroleum ether gave 3-butyryl-4-chloro-8-methoxyquinoline (5.5 g. 58.5%), m.p. 114°-116°.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureWhen cool
  3. additionthe mixture was poured onto ice
  4. extractionextracted with dichloromethane
  5. customEvaporation and crystallisation from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-25a1860ef39e48d9ba9cfa325e1f7807
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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