Phosphorus oxychloride → Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

HRID 495476Notes

Reaction equation

HRID 495476 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](O)=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:21]>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:21])=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469633HCID 178469633, compound

Product 1

HCID 728976Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Procedure

7-Methoxy-4-hydroxy-3-ethoxycarbonylquinoline (Step A, 21 g, 0.08 mol) and POCl3 (100 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 then by a minimum amount of MeOH to give 7-methoxy-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

Sources & evidence

ORD record
ord-4cf8ffa3686f4d47b6f619037dd660ee
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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