Nitric Acid → 4-Hydroxy-3-nitro-2(1H)-quinolinone

Participants

Reaction Conditions

Reaction Steps

Fuming nitric acid (262 mL) was added at about 20° C. to a suspension of 4-hydroxy-2(1H)-quinolinone (1.0 Kg) in acetic acid (7.57 L). The mixture was heated at 40° C. for 2.5 h. The resulting solution was cooled to about 20° C. and poured into 8 L of water. The resulting solution was stirred for 20 min, filtered, washed with water until the filtrate was neutral, and dried. The product 4-hydroxy-3-nitro-2(1H)-quinolinone was isolated in 98% yield and showed only one spot upon analysis by thin layer chromatography (silica gel, 20:80 (V/V) chloroform in methanol).

Provenance & Evidence