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

HRID 1507412Notes

Reaction equation

HRID 1507412 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-e249c3ec165d418983ae93d2feec173c
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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