Reaktion #308715

Reaktionsgleichung

phosphorous oxychloride

7-benzyloxy-3-nitroquinolin-4-ol

→

7-benzyloxy-4-chloro-3-nitroquinoline

Ausbeute 94.2%

Lösungsmittel

dichloromethane

N,N-Dimethylformamide

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe addition
2. 2
   Temperaturcooled to ambient temperature
3. 3
   workup.STIRRINGwith stirring
4. 4
   SonstigeA tan precipitate formed
5. 5
   Sonstigewhich was isolated by filtration
6. 6
   TrocknenThe resulting solution was dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure

Vorschrift

N,N-Dimethylformamide (DMF) (100 mL) was cooled to 0° C., and phosphorous oxychloride (27.5 mL, 0.295 mol) was added dropwise. The resulting solution was stirred for 25 minutes and then added dropwise to a mixture of 7-benzyloxy-3-nitroquinolin-4-ol (72.87 g, 0.2459 mol) in DMF (400 mL). Following the addition, the reaction was heated at 100° C. for 5 minutes, cooled to ambient temperature, and poured into ice water with stirring. A tan precipitate formed, which was isolated by filtration and dissolved in dichloromethane. The resulting solution was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 72.9 g of 7-benzyloxy-4-chloro-3-nitroquinoline as a light brown solid.

Quelle