2-Chloro-6-nitroquinoline → Ammonia

Participants

Reaction Steps

A mixture of 2-chloro-6-nitroquinoline [Lee B S, Lee B C, Jun J-G and Chi D Y; Heterocycles 1998 48 (12) 2637-2641] (2.1 g; 10 mmol), tert-butyl-(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.0 g; 10 mmol) and dioxane (50 ml) was stirred at reflux for 20 hours. The solvent was evaporated. Aqueous sodium hydroxide (50 ml; 1 M) was added, followed by extraction with diethyl ether (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 1.6 g (43%).

Provenance & Evidence