Thionyl Chloride → 6-Chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride

HRID 638286Notes

Reaction equation

HRID 638286 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[CH:6]=[C:5]2[C:19]([OH:21])=O.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[CH:6]=[C:5]2[C:19]([Cl:24])=[O:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11330936-chloro-2-(4-methylphenyl)quinoline-4-carboxylic acid

Product 1

HCID 202536626-Chloro-2-(4-methylphenyl)-4-quinolinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 28.4 g of 6-chloro-2-(4-methylphenyl)-4-quinolinecarboxylic acid, 100 ml of thionyl chloride, and 200 ml of toluene was stirred and heated under reflux for 1.5 hr. The reaction mixture was then concentrated in vacuo, the residue was treated with more toluene, and the mixture again concentrated in vacuo. The residue was recrystallized from 300 ml of heptane to give 17.7 g of the above-named compound as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hr
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. additionthe residue was treated with more toluene
  5. concentrationthe mixture again concentrated in vacuo
  6. customThe residue was recrystallized from 300 ml of heptane

Sources & evidence

ORD record
ord-42a32148d24b4982b783a122129ca0c1
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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