Piperidine → 5,7-diethyl-3-methyl-1,6-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-2,6-diethylpyridine-3-carbaldehyde (2.0 g), piperidine (0.5 ml) and diethyl methylmalonate (3.0 ml) was heated together at 120° C. for 24 hours. The mixture was then purified by flash chromatography, eluting with ether, to give 5,7-diethyl-3-methyl-1,6-naphthyridin-2(1H)-one as a solid (0.265 g); m.p. 163°-166° C. dec. (after recrystallisation from acetone); NMR (d6 -DMSO): 1.22(t, 3H), 1.24(t, 3H), 2.11(s, 3H), 2.71(q, 2H), 2.99(q, 2H), 6.88(s, 1H), 7.96(s, 1H), 11.84(broad, 1H); mass spectrum (CI, ammonia): 217 (M+H)+ ; microanalysis, found: C, 72.3; H, 7.4; N, 13.1%; C13H16N2O requires: C, 72.2; H, 7.5; N, 13.0%.

Provenance & Evidence