Ethyl cyanoacetate → HCID 10157303, compound

Participants

Reaction Steps

5-Amino-1-ethyl-1,2-dihydropyrazol-3-one (0.13 g, 1 mmol), prepared by the method of (A. Weisberger and A. Porter, J. Amer. Chem. Soc, (1944) 66,1849) from ethylhydrazine and ethyl cyanoacetate, 3-bromo-4-fluorobenzaldehyde (0.2 g, 1 mmol), and 1,3-cyclopentanedione (0.1 g, 1 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was cooled and the resulting precipitate was filtered off to provide 0.23 g (58%) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 1.22 (t, 3H), 2.28 (t, 2H), 2.68 (m, 2H), 3.82 (q, 2H), 4.7 (s, 1H), 7.17 (m, 1H), 7.2 (t, 1H), 7.4 (dd,1H), 9.64 (bs, 1H), 10.4 (s, 1H); MS (ESI−) m/z 392 (M−H)−; Anal. calcd for C17H15N3BrFO2.0.5H2O: C, 50.89; H, 4.02; N, 10.47. Found: C, 50.85; H, 3.72; N, 10.25.

Provenance & Evidence