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

HRID 1382339Notes

Reaction equation

HRID 1382339 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-02d9e05bfcb54c598e3c405acc97cdc4
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

Loading…