Sodium Hydroxide → 4-Chloro-2-(4-chlorophenyl)quinoline

HRID 638263Notes

Reaction equation

HRID 638263 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16](O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+]>>[Cl:21][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178515604HCID 178515604, compound

Product 1

HCID 112195464-Chloro-2-(4-chlorophenyl)quinoline

Procedure

A mixture of 21.6 g of 2-(4-chlorophenyl)-4-quinolinol and 46 ml of phosphorus oxychloride was heated under reflux for 45 min., cooled to room temperature, and poured carefully onto 750 ml of ice water. This mixture was neutralized with 146 ml of 50% sodium hydroxide and extracted with 600 ml of methylene chloride in three portions. The extracts were combined, filtered through 15 g of Florisil, and concentrated in vacuo to leave 19.35 g of the above-named compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 min.
  3. extractionextracted with 600 ml of methylene chloride in three portions
  4. filtrationfiltered through 15 g of Florisil
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-881f9a55dde4467b95677c5dc24b5e13
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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