1,3-Cyclohexanedione → HCID 13533641, compound

Participants

Reaction Steps

A mixture of N-methyl-imidazole-2-carboxaldehyde (4.9 g, 0.045 mole), 1,3-cyclohexandione (5.8 g, 0.045 mole), and ethyl-3-aminocrotonate (5.04 g, 0.045 mole), in 50 mL of absolute ethanol was refluxed for 24 hours. The reaction mixture was cooled and the separated solid was filtered and recrystallized from a hexane-ethylacetate (1:1) mixture to afford 5.2 g (37% yield) of the title compound, m.p. 271°-272° C.; MS, m/e 315 (M+); NMR (CDCl3) δ 1.0 (t, 3 H, CCH 3), 1.5-2.4 (m, 6 H, cyclohexanone), 2.5 (s, 3 H, =CCH3), 3.9-4.1 (q, 2 H, CH2C), 4.0 (s, 3 H, NCH3), 5.2 (s, 1 H, dihydropyridine-H), 6.3 (d, 1 H, imidazole-H), 6.5 (d, 1 H, imidazole-H) and 9.5 (s, 1 H, NH).

Provenance & Evidence