Reaktion #7567

Reaktionsgleichung

7-benzyloxy-4-hydroxy-6-methoxycinnoline

thionyl chloride

DMF

→

7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 1 hour
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigeexcess thionyl chloride was removed by evaporation
4. 4
   Sonstigeazeotroped with toluene
5. 5
   SonstigeThe residue was triturated with ether
6. 6
   Filtrationfiltered off
7. 7
   Waschenwashed with ether
8. 8
   Sonstigedried under vacuum

Vorschrift

The starting material, 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride, was obtained by heating a solution of 7-benzyloxy-4-hydroxy-6-methoxycinnoline (11 g, 39 mmol) in thionyl chloride (180 ml) containing DMF (1 ml) at reflux for 1 hour. After cooling, excess thionyl chloride was removed by evaporation and azeotroped with toluene. The residue was triturated with ether, filtered off, washed with ether and dried under vacuum to give 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride as a cream solid (13.6 g, quantitative).

Quelle