Thionyl Chloride → Ethyl 4,6-dichloroquinoline-3-carboxylate

HRID 1395280Notes

Reaction equation

HRID 1395280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]2O.S(Cl)([Cl:20])=O>>[Cl:20][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178469539HCID 178469539, compound

Product 1

HCID 1479087Ethyl 4,6-dichloroquinoline-3-carboxylate

Procedure

A mixture of 45.2 g. of 6-chloro-4-hydroxyquinoline-3-carboxylic acid, ethyl ester (0.18 mol.) and 250 ml. of thionyl chloride is refluxed for 20 hours. The excess thionyl chloride is then removed in vacuo, the residue treated with 200 ml. of water and the ester is extracted with ether. After washing the ethereal extract twice with water, it is dried with Na2SO4 and the solvent distilled off. The residual 4,6-dichloroquinoline-3-carboxylic acid, ethyl ester is triturated with petroleum ether (40°-60°), filtered and dried. Yield: 45.3 g. (93%); m.p. 87°-88°.

Workup

  1. additionA mixture of 45.2 g
  2. customThe excess thionyl chloride is then removed in vacuo
  3. additionthe residue treated with 200 ml
  4. extractionof water and the ester is extracted with ether
  5. washAfter washing the ethereal
  6. extractionextract twice with water, it
  7. dry with materialis dried with Na2SO4
  8. distillationthe solvent distilled off
  9. customThe residual 4,6-dichloroquinoline-3-carboxylic acid, ethyl ester is triturated with petroleum ether (40°-60°)
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-b164af05fc0a40b7bca11c9f4528abd8
Source dataset
uspto-grants-1980_05
Patent number
US04202985

Reaction notes

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