Nitric Acid → 4-Hydroxy-3-nitro-5,6,7,8-tetrahydroquinolin-2(1H)-one

Participants

Reaction Steps

A solution of 4-hydroxy-5,6,7,8-tetrahydrocarbostyril (1.70g; 0.0103 mole) and concentrated nitric acid (2.5 ml; d 1.42), in glacial acetic acid (10 ml) was heated at 100° C till the oxides of nitrogen were evolved and rapidly cooled in ice. Water (40 ml) was added to the red solution to precipitate the yellow-orance 3-nitro derivative. After filtration, thorough washing with water and recrystallisation from acetic acid - ethanol the product had m.p. 241° (d).

Provenance & Evidence