Ammonium Hydroxide → 5-Chloro-6-methoxy-4-methyl-8-nitroquinoline

Participants

Reaction Steps

A solution of the 5-hydroxyquinoline IV (5.25 g, 0.022 mol) in phosphorus oxychloride (75 mL) was heated at 80° for 2 hours. The reaction mixture was poured onto ice and basified with excess ammonium hydroxide. The tan solid was filtered to give 5.8 g of crude product. This material was purified via column chromatography over silica gel and elution with chloroform. The fast-moving yellow band was collected and concentrated to give 3.9 g (69%) of the title compound, mp 167°-169°. Crystallization from ethanol did not raise the melting point. The crude material can also be purified by sublimation.

Provenance & Evidence