Reaktion #7581

Reaktionsgleichung

4-hydroxy-7-methoxycinnoline

thionyl chloride

DMF

→

4-chloro-7-methoxycinnoline hydrochloride

Ausbeute 97.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux, for 1 hour
2. 2
   SonstigeAfter removing excess thionyl chloride
3. 3
   Sonstigeby evaporation
4. 4
   Sonstigeazeotroping with toluene
5. 5
   SonstigeThe residue was triturated with ether
6. 6
   Filtrationfiltered off
7. 7
   Waschenwashed with ether

Vorschrift

The starting material 4-chloro-7-methoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-7-methoxycinnoline (352 mg, 2 mmol), (prepared as described in J. Chem. Soc. 1955, 2100), in thionyl chloride (3.5 ml) containing DMF (20 μl) at reflux, for 1 hour. After removing excess thionyl chloride by evaporation and azeotroping with toluene. The residue was triturated with ether, filtered off and washed with ether to give 4-chloro-7-methoxycinnoline hydrochloride as a yellow solid (450 mg, 97%).

Quelle