Phosphorus oxychloride → Ethyl 4,7-dichloroquinoline-3-carboxylate

HRID 1395284Notes

Reaction equation

HRID 1395284 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 345422Ethyl 7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 12256460Ethyl 4,7-dichloroquinoline-3-carboxylate

Procedure

A mixture of 30 g. of 7-chloro-4-hydroxyquinoline-3-carboxylic acid, ethyl ester, m.p. 299°-301°, (0.12 mol.) and 250 ml. of phosphorus oxychloride is refluxed for 4.5 hours. After removing the excess phosphorus oxychloride, the residue is triturated with water and dissolved in ether. The ethereal solution is washed with aqueous sodium carbonate (5%) and water, dried with sodium sulfate and the solvent is removed. The residual 4,7-dichloroquinoline-3-carboxylic acid, ethyl ester is triturated with petroleum ether (40°-60°), filtered off and dried; yield: 22 g. (68%); m.p. 81°-82°.

Workup

  1. additionA mixture of 30 g
  2. customAfter removing the excess phosphorus oxychloride
  3. customthe residue is triturated with water
  4. dissolutiondissolved in ether
  5. washThe ethereal solution is washed with aqueous sodium carbonate (5%) and water
  6. dry with materialdried with sodium sulfate
  7. customthe solvent is removed
  8. customThe residual 4,7-dichloroquinoline-3-carboxylic acid, ethyl ester is triturated with petroleum ether (40°-60°)
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-6159140babe843a0a3acd6277a44d7c9
Source dataset
uspto-grants-1980_05
Patent number
US04202985

Reaction notes

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