Ammonia → 6-Benzyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridine

Participants

Reaction Conditions

Reaction Steps

3,5-Dinitro-1-methyl-2-pyridone (1.99 g; 10 mmol) [prepared according to E. Matsumura, M. Ariga and Y. Tohda, Bull. Chem. Soc. Japan, 1979, 52, 2413 ] was added to a solution of ammonia in methanol (1.1M; 100 ml; 110 mmol) and then treated with 1-benzyl-4-piperidone (2.27 g; 12 mmol). The resulting mixture was heated at 60° C. for 5 h, cooled to room temperature and evaporated to dryness in vacuo. The residue was purified by chromatography through SiO2 eluting with 50% ethyl acetate/60-80° pet. ether to give the title compound (2.5 g; 93%). Recrystallisation from ethyl acetate −60-80° petroleum ether gave the title compound as a pale yellow, microcrystalline solid, mp 108° C.

Provenance & Evidence