5-Nitroquinoline → 5-Nitroquinolin-8-amine

Participants

Reaction Conditions

Reaction Steps

To a five liter round bottom flask fitted with an air stirrer, condenser, addition funnel, thermometer and hot water bath were charged 40 g. (.23 mole) 5-nitroquinoline and 100 g. (1.44 mole) hydroxylamine hydrochloride. Then 1950 ml. of 95% EtOH was added and the solids dissolved after which 200 g. KOH in 1200 ml. MeOH was added over a 50 minute period at 54°-57° C. The mixture was allowed to stir at 55° C. for an additional hour and then dumped into 10 liters of water, allowed to cool and filtered. An orange solid was crystallized out of 95% ethanol. Such product was 8-amino-5-nitroquinoline.

Provenance & Evidence