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

HRID 2280498Notes

Reaction equation

HRID 2280498 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 desired 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-23c1dbef4b9e420e8eed018a67c2b0c2
Source dataset
uspto-grants-2015_09
Patent number
US09139528B2

Reaction notes

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