1,3-Cyclopentanedione → HCID 9925263, compound

Participants

Reaction Steps

5-Amino-1,2-dihydropyrazol-3-one (0.15 g, 1.5 mmol), 3-bromo-4-fluorobenzaldehyde (0.31 g, 1.5 mmol), and 1,3-cyclopentanedione (0.15 g, 1.5 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate:formic acid:water (18:1:1) to provide 0.125 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.22 (t, 2H), 2.61 (m, 2H), 4.73 (s,1H), 7.15 (m, 1H), 7.2 (m, 1H), 7.4 (dd, 1H), 9.75 (s, 1H), 10.21 (s, 1H), 11.3 (bs, 1H); MS (ESI) m/z 362 (M−H)−; Anal. calcd for C15H, N3BrFO2.0.5H2O: C, 48.28; H, 3.24; N, 11.26Found: C, 48.88; H, 3.29; N, 10.83.

Provenance & Evidence