HCID 178427290, compound → 4-Chloro-3-(4-methyl-benzenesulfonyl)-quinoline

HRID 561038Notes

Reaction equation

HRID 561038 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2O)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O(Cl)[Cl:23].[P+5]>>[Cl:23][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 178427290HCID 178427290, compoundHCID 178479711HCID 178479711, compound

Product 1

HCID 670001244-Chloro-3-(4-methyl-benzenesulfonyl)-quinolineYield 90%

Conditions

Temperature
2.5 °C

Procedure

A mixture of 3-(4-methyl-benzenesulfonyl)-quinolin-4-ol (0.24 g, 0.8 mmol) and phosphorus(V) oxychloride (15 ml) was refluxed for 5 hours. Phosphorus(V) oxychloride was distilled off, and the residue was poured onto ice. The slurry was stirred for 2 hours at 0-5° C., neutralized with sodium carbonate and extracted with chloroform (50 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to give 0.23 g of the title compound in 90% yield.

Workup

  1. temperaturewas refluxed for 5 hours
  2. distillationPhosphorus(V) oxychloride was distilled off
  3. additionthe residue was poured onto ice
  4. extractionextracted with chloroform (50 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-066976949b8c4fda9ad5580afc92c632
Source dataset
uspto-grants-2011_11
Patent number
US08063220B2

Reaction notes

Loading…