4-Nitrophenol → 6-Methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of p-methoxyaniline (24.6 g, 0.2 mol), ferrous sulfate (8.34 g, 0.03 mol), glycerol (73.6 g, 60 mL), p-nitrophenol (16.68 g, 0.12 mol), and concentrated sulfuric acid (10 mL) was heated gently to 70° C. Then a second portion of concentrated sulfuric acid (25 mL) was added dropwise to the reaction mixture and it was stirred at reflux for 8 hours. After cooling down to room temperature, the reaction mixture was basified to pH=5.5 with 15% aqueous sodium hydroxide solution in an ice bath. The resulting precipitate was filtered, dried and 16 g of 6-methoxy-quinoline was obtained as a yellow solid (50% yield).

Provenance & Evidence