Phosphorus oxychloride → HCID 10384366, compound

HRID 1534479Notes

Reaction equation

HRID 1534479 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([CH2:17][O:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:29])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:29])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10043403HCID 10043403, compound

Product 1

HCID 10384366HCID 10384366, compound

Procedure

A solution of 3-isobutyryl-8-(benzoyloxymethyl)-4(1H)-quinolone (11.81 g, 29.9 mmol) in phosphoryl chloride (100 ml) was heated at reflux for 2.5 hours, then the excess phosphoryl chloride evaporated. Water was added and the product extracted into a mixture of dichloromethane and isopropyl alcohol. Drying and evaporation of the organic layer gave crude 3-isobutyryl-4-chloro-8-(benzoyloxymethyl)quinoline (12.0 g), contaminated with isopropyl alcohol. This was used without further purification.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customthe excess phosphoryl chloride evaporated
  3. additionWater was added
  4. extractionthe product extracted into a mixture of dichloromethane and isopropyl alcohol
  5. customDrying
  6. customevaporation of the organic layer

Sources & evidence

ORD record
ord-7468ee6dbfc44bb5a4e15b9e208270c5
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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