4-Aminophenol → 6-Hydroxyquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-aminophenol (44.7 g, 0.41 mol), ferrous sulfate (14 g, 0.05 mol), glycerol (120 mL, 1.65 mol), p-nitrophenol (33.3 g, 0.24 mol), and concentrated sulfuric acid (20 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 the mixture 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 25 g of quinolin-6-ol was obtained as a yellow solid (42% yield).

Provenance & Evidence