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

HRID 1410621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410621
[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

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 669801226-methoxy-3-(trifluoromethyl)quinolin-2(1H)-one

Produkt 1

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

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5b96b4f4d71441dc9f5437879440be32
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921562B2

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