Phosphorus oxychloride → Ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate

HRID 1007872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007872
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:18][Cl:19])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8](=O)[NH:9]2)=[CH:4][C:3]=1[O:20][CH3:21].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:8]1[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]([CH2:18][Cl:19])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([O:20][CH3:21])[CH:4]=2)[N:9]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 21892028HCID 21892028, Verbindung

Produkt 1

HCID 21891992Ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate

Versuchsvorschrift

A suspension of ethyl 7-chloro-4-(chloromethyl)-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate (116.7 g, 50 mmol) in phosphoryl chloride (100 ml) is heated to reflux for 6 hours. The phosphoryl chloride is distilled off. The residue is taken up in water and agitation is carried out for 30 min. The precipitate is filtered out and washed with water until neutrality. The precipitate is taken up in dichloromethane and with a saturated solution of sodium chloride. After filtering through a bed of celite the filtrate is decanted. The organic phase is washed again with a saturated solution of sodium chloride, followed by drying over magnesium sulphate, filtering and evaporating under reduced pressure. 15.88 g of a brown oil is obtained.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. distillationThe phosphoryl chloride is distilled off
  4. filtrationThe precipitate is filtered out
  5. washwashed with water until neutrality
  6. filtrationAfter filtering through a bed of celite the filtrate
  7. customis decanted
  8. washThe organic phase is washed again with a saturated solution of sodium chloride
  9. dry with materialby drying over magnesium sulphate
  10. filtrationfiltering
  11. customevaporating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-962d41b651f4449184a31fe40ea49866
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797715B1

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