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

HRID 1382287Notes

Reaction equation

HRID 1382287 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([CH3:17])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:20])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:20])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 103765253-butyryl-8-methyl-4(1H)-quinolone

Product 1

HCID 100376273-Butyryl-4-chloro-8-methylquinoline

Procedure

3-Butyryl-8-methyl-4(1H)-quinolone (20 g) and phosphoryl chloride (80 ml) were heated under reflux for 45 minutes. Excess phosphoryl chloride was evaporated in vacuo, the residue poured onto ice and neutralised with sodium hydrogen carbonate. Extraction with dichloromethane, drying and evaporation gave 3-butyryl-4-chloro-8-methylquinoline (20 g) as a brown oil, which solidified at -15° C. but melted below room temperature. This was used without further purification.

Workup

  1. temperatureunder reflux for 45 minutes
  2. customExcess phosphoryl chloride was evaporated in vacuo
  3. additionthe residue poured onto ice and neutralised with sodium hydrogen carbonate
  4. extractionExtraction with dichloromethane
  5. customdrying
  6. customevaporation

Sources & evidence

ORD record
ord-8e22605750e74186803b19d6d8b08d04
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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