Phosphorus oxychloride → HCID 22139692, compound

HRID 457001Notes

Reaction equation

HRID 457001 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=O)[NH:10]2.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:5]=2[O:4][C:3]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:2]=2[F:1])[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22139754HCID 22139754, compound

Product 1

HCID 22139692HCID 22139692, compoundYield 87.5%

Procedure

A solution of 5-(2,4-difluoro-phenoxy)-6-methoxy-1H-quinolin-2-one derivative (0.3 g) in 10 mL of POCl3 was refluxed for 1.5 hours. POCl3 was removed under vacuum, the residue was stirred with saturated aqueous sodium bicarbonate solution, the product was extracted with methylene chloride, and the organic layer was dried (MgSO4). Solvent removal gave 0.28 g (87.5%) of 2-chloro-5-(2,4-difluoro-phenoxy)-6-methoxy-quinoline as pure white crystals.

Workup

  1. customPOCl3 was removed under vacuum
  2. extractionthe product was extracted with methylene chloride
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customSolvent removal

Sources & evidence

ORD record
ord-1b12ab327dcd4e97980db5859ec6b871
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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