Phosphorus oxychloride → 3-Butyryl-4-chloro-8-(4-methoxybenzoyloxymethyl)quinoline

HRID 1647440Notes

Reaction equation

HRID 1647440 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([CH2:17][O:18][C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:31])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:31])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 103175623-butyryl-8-(4-methoxybenzoyloxymethyl)-4(1H)-quinolone

Product 1

HCID 104534453-Butyryl-4-chloro-8-(4-methoxybenzoyloxymethyl)quinoline

Procedure

A solution of 3-butyryl-8-(4-methoxybenzoyloxymethyl)-4(1H)-quinolone (5.75 g, 15.1 mmol) in phosphoryl chloride (75 ml) was heated at reflux for 30 minutes, the phosphoryl chloride evaporated in vacuo, the residue poured onto ice, neutralised with sodium bicarbonate, and extracted into dichloromethane. Drying, evaporation, and trituration with ether gave the crude 3-butyryl-4-chloro-8-(4-methoxy-benzoyloxymethyl)quinoline, which was used without further purification.

Workup

  1. temperatureat reflux for 30 minutes
  2. customthe phosphoryl chloride evaporated in vacuo
  3. additionthe residue poured onto ice
  4. extractionextracted into dichloromethane
  5. customDrying
  6. customevaporation, and trituration with ether

Sources & evidence

ORD record
ord-ce59032f6c844ce0ad16abb5e6e1ce34
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

Loading…