Phosphorus oxybromide → Methyl 4-bromo-3-chloroquinoline-6-carboxylate

HRID 533416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533416
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1O)=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=2.P(Br)(Br)([Br:19])=O>>[Br:19][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[N:4]=[CH:3][C:2]=1[Cl:1]

Komponenten

3

Edukt 2

HCID 24613Phosphorus oxybromideHCID 178497322HCID 178497322, Verbindung

Produkt 1

HCID 67773454Methyl 4-bromo-3-chloroquinoline-6-carboxylateAusbeute 56,1 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of methyl 3-chloro-4-hydroxyquinoline-6-carboxylate (600 mg) and phosphoryl bromide (868 mg) was heated under stirring in an oil bath at 130° C. for 6 hours. Ice-water was added, followed by neutralization with saturated aqueous sodium bicarbonate and extraction with ethyl acetate. The organic layer was washed with water, dried, and concentrated under reduced pressure to obtain methyl 4-bromo-3-chloroquinoline-6-carboxylate (426 mg).

Aufarbeitung

  1. temperaturewas heated
  2. extractionfollowed by neutralization with saturated aqueous sodium bicarbonate and extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-667da52522404e4a9fded3d4372f430a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853242B2

Notizen zur Reaktion

Wird geladen…