Phosphorus oxychloride → Ethyl 4-chloro-6-(trifluoromethoxy)quinoline-3-carboxylate

HRID 495474Notes

Reaction equation

HRID 495474 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]2O.O=P(Cl)(Cl)[Cl:24]>>[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]2[Cl:24]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469603HCID 178469603, compound

Product 1

HCID 22326848Ethyl 4-chloro-6-(trifluoromethoxy)quinoline-3-carboxylate

Procedure

6-Trifluoromethoxy-4-hydroxy-3-ethoxycarbonylquinoline (3 g, 10 mmol) and POCl3 (8 mL) were mixed together and the mixture was heated at reflux for 6 h. The excess POCl3 was removed under vacuum. The solid residue was suspended in ice-cold 1N NaOH and the mixture was stirred for 15 min. The solid was filtered off, washed several times with water and dried over P2O5 to give 6-trifluoromethoxy-4-chloro-3-ethoxycarbonylquinoline as an off-white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h
  3. customThe excess POCl3 was removed under vacuum
  4. filtrationThe solid was filtered off
  5. washwashed several times with water
  6. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-3ab95b18c39046478a555d1af1a42796
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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