Phosphorus oxychloride → 2-Chloro-6-methoxyquinoline

HRID 456986Notes

Reaction equation

HRID 456986 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2282682-Hydroxy-6-methoxyquinoline

Product 1

HCID 836472-Chloro-6-methoxyquinoline

Procedure

A solution of 1.7 g of 6-methoxy-2(1H)-quinolone (10 mmoles) in 25 mL POCl3 was refluxed for 2 hours. The reagent was removed under reduced pressure and the resulting gum dissolved in CH2Cl2. The solution was washed with aqueous NaHCO3 to remove remaining acid, dried over MgSO4, and then evaporated to afford 2-chloro-6-methoxy-quinoline as a solid.

Workup

  1. customThe reagent was removed under reduced pressure
  2. dissolutionthe resulting gum dissolved in CH2Cl2
  3. washThe solution was washed with aqueous NaHCO3
  4. customto remove
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-778d75503a8d4efe9209071536284655
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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