Reaktion #318727

Reaktionsgleichung

water

8-(4-hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline

sodium nitrate

lanthanum nitrate

→

8-(4-hydroxy-3-nitrophenylthio)-5,6,7,8-tetrahydroquinoline

Ausbeute 31.9%

Lösungsmittel

ether

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with chloroform
2. 2
   SonstigeRemoval of solvent
3. 3
   workup.WAITleft a yellow oil which
4. 4
   Sonstigewas purified by flash chromatography (Kieselgel 60; 10% ethyl acetate in dichloromethane)

Vorschrift

15.0 g (58 mmol) of 8-(4-hydroxyphenylthio)-5,6,7,8-tetrahydroquinoline in 90 ml of ether were added dropwise to a stirred solution of 4.96 g (58 mmol) of sodium nitrate and 0.25 g (58 mmol) of lanthanum nitrate in 60 ml of 5.5N hydrochloric acid at 0° to 5° C. in an ice-bath. Stirring was then continued under nitrogen for 24 hours, after which water was added and the mixture was extracted with chloroform. Removal of solvent left a yellow oil which was purified by flash chromatography (Kieselgel 60; 10% ethyl acetate in dichloromethane) to obtain 5.6 g (20%) of 8-(4-hydroxy-3-nitrophenylthio)-5,6,7,8-tetrahydroquinoline as yellow crystals (from ethanol).

Quelle