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

HRID 1885173Notes

Reaction equation

HRID 1885173 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([C:17](=[O:19])[CH3:18])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:22])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:22])=[CH:13][CH:12]=[CH:11][C:10]=2[C:17](=[O:19])[CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 103777553-butyryl-8-acetyl-4(1H)-quinolone

Product 1

HCID 102654513-Butyryl-4-chloro-8-acetylquinoline

Procedure

A solution of 3-butyryl-8-acetyl-4(1H)-quinolone (8.4 g) in phosphoryl chloride (30 ml) was heated at reflux for 1 hour, then poured onto ice and the product extracted into ether. Drying and evaporation gave crude 3-butyryl-4-chloro-8-acetylquinoline as a dark solid, which was used without further purification.

Workup

  1. temperatureat reflux for 1 hour
  2. additionpoured onto ice
  3. extractionthe product extracted into ether
  4. customDrying
  5. customevaporation

Sources & evidence

ORD record
ord-820a2d6e82fa4f3eba8d0efc0e662fb3
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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