Reaktion #7562

Reaktionsgleichung

4-hydroxy-6-methoxy-7-(2-methoxyethoxy)cinnoline

thionyl chloride

DMF

→

4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline

Ausbeute 74.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter dilution with toluene, the mixture was evaporated to dryness
2. 2
   FiltrationThe resulting solid was filtered off
3. 3
   Waschenwashed with ether
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate
5. 5
   WaschenThe ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate solution
6. 6
   Trocknenbrine, dried (MgSO4)
7. 7
   Sonstigethe solvent evaporated
8. 8
   SonstigeThe residue was purified by flash chromatography

Vorschrift

The starting material 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline was obtained by heating a solution of 4-hydroxy-6-methoxy-7-(2-methoxyethoxy)cinnoline (7.8 g, 0.031 mol) in thionyl chloride (130 ml) containing DMF (0.8 ml) at 80° C. for 2 hours. After dilution with toluene, the mixture was evaporated to dryness. The resulting solid was filtered off, washed with ether, and then dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate solution and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/ethyl acetate (1/9) as eluent to give 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (6.2 g, 74%).

Quelle