Phosphorus oxychloride → 2-Chloro-6-methoxy-3-(trifluoromethyl)quinoline

HRID 1627689Notes

Reaction equation

HRID 1627689 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)[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6]2.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:8]1[C:7]([C:14]([F:17])([F:16])[F:15])=[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 669801226-methoxy-3-(trifluoromethyl)quinolin-2(1H)-one

Product 1

HCID 866899362-Chloro-6-methoxy-3-(trifluoromethyl)quinolineYield 94%

Procedure

A solution of 6-methoxy-3-(trifluoromethyl)quinolin-2(1H)-one (4.60 g, 18.9 mmol) in POCl3 (30 mL) was refluxed for 2.5 hours. The solvent was removed under reduced pressure and the residue was neutralized by 2M NaOH to pH 7. An EtOAc workup was followed by removal of volatiles under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc=15/1) to give the product (4.60 g, yield 94%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customAn EtOAc workup was followed by removal of volatiles under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (PE/EtOAc=15/1)

Sources & evidence

ORD record
ord-ed76d39c4b17411c99d73d07a9c28526
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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