Nitric Acid → Quinoline, 8-fluoro-5-nitro-

Participants

Reaction Steps

15 ml of nitric acid were added with stirring at -5° C. to 30 ml of concentrated sulfuric acid and then 16 g of 8-fluoroquinoline were added thereto with stirring over 30 minutes at -5° to 0° C. The mixture was stirred at 0° C. for three hours and was then allowed to return to room temperature. The mixture was stirred at room temperature for two hours and was then poured into a mixture of water and ice. The mixture was vacuum filtered and the product was suspended in water. The mixture was made alkaline by addition of 10% sodium carbonate solution and was extracted with methylene chloride. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 12 g of 5-nitro-8-fluoro-quinoline melting at 132°-133° C.

Provenance & Evidence