Phosphorus oxychloride → 1-(4-Chloro-8-methoxy-3-quinolinyl)ethanone

HRID 1382307Notes

Reaction equation

HRID 1382307 reaction equation
[C:1]([C:4]1[C:13](=O)[C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:19])=O>>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[Cl:19])=[CH:11][CH:10]=[CH:9][C:8]=2[O:15][CH3:16])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10262793HCID 10262793, compound

Product 1

HCID 100143131-(4-Chloro-8-methoxy-3-quinolinyl)ethanone

Procedure

3-Acetyl-8-methoxy-4(1H)-quinolone (4.23 g, 19 mmol) and phosphorus oxychloride (150 ml) were heated under reflux for 45 minutes, evaporated to small volume in vacuo, poured onto ice, and the mixture adjusted to pH 4 with sodium bicarbonate. Extraction with chloroform, drying and evaporation of the organic solution gave crude 3-acetyl-4-chloro-8-methoxyquinoline as a dark coloured oil (7.9 g), which was used without purification.

Workup

  1. temperatureunder reflux for 45 minutes
  2. customevaporated to small volume in vacuo
  3. additionpoured onto ice
  4. extractionExtraction with chloroform
  5. customdrying
  6. customevaporation of the organic solution

Sources & evidence

ORD record
ord-40ac11edc0ee40bf8259deefd3ab5374
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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