4-Nitrophenol → Quinoline, 6-fluoro-8-nitro-

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-2-nitro-phenylamine (15 g, 96 mmol) was added to a mixture of 4-nitrophenol (9.5 g, 144 mmol) and glycerol (27 ml), then concentrated sulphuric acid (8.3 ml, 154 mmol) was added dropwise. The mixture was stirred at 130° C. for 4 hours. For the workup, the reaction mixture was cooled to room temperature, then poured into ice-water. The precipitate was filtered and the aqueous phase was made basic with sodium hydroxide (15% solution). There were obtained 2.0 g (11%) of 6-fluoro-8-nitro-quinoline as a brown solid; (calculated) C9H5FN2O2 [192.2]; (found) [M+H]+=193.

Provenance & Evidence