Ethanol → HCID 13533643, compound

Participants

Reaction Steps

To a stirred mixture of 2.3 g (0.02 mole) of 1,3-cyclohexandione, ethyl-4,4,4-trifluoroacetoacetate (3.3 g, 0.02 mole) and ammonium acetate (4.9 g, 0.4 mole) in 50 mL of absolute ethanol, (2.0 g, 0.02 mole) of N-methylimidazole-2-carboxaldehyde was added. The reaction mixture was refluxed for 24 hours and allowed to cool to room temperature. The solvent was evaporated in vacuo, and the residue was separated by high performance liquid chromatography (30% methanol-ethylacetate mixture as the eluent) to afford 0.5 g (7% yield ) of the title compound, m.p. 197°-198° C.; MS, m/e 369 (M+); NMR (CDCl3) δ1.0 (t, 3 H, CCH3), 1.5-2.4 (m, 6 H, cyclohexenone), 3.7 (s, 3 H, NCH3), 4-4.1 (q, 2 H, CH2C), 5.0 (s, 1 H, dihydropyridine-H), 6.5 (d, 1 H, imidazole-H), 6.8 (d, 1 H, imidazole-H) and 9.6 (s, 1 H, NH).

Provenance & Evidence