1,3-Cyclohexanedione, 4,4-dimethyl- → HCID 10202275, compound

Participants

Reaction Steps

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.23 g, 2 mmol), 3-bromo-4-fluorobenzaldehyde (0.4 g, 2 mmol), and 4,4-dimethyl-1,3-cyclohexanedione (0.28 g, 2 mmol) in ethyl alcohol (3 mL) were heated at 80° C. in a sealed tube for 2 days. The reaction mixture was cooled and the resulting precipitate was filtered off and washed with ethyl acetate to provide 0.55 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 0.98 (s, 3H), 1.78 (t, 2H), 2.63 (m, 2H), 3.43 (s, 3H), 4.83 (s, 1H), 7.11 (m, 1H), 7.17 (t, 1H), 7.33 (dd, 1H), 9.53 (s, 1H), 9.66 (s, 1H); MS (ESI−) m/z 420 (M−H)−; Anal. calcd for C19H19N3BrFO2: C, 54.30; H, 4.56; N, 10.00. Found: C, 54.29; H, 4.61; N, 9.97.

Provenance & Evidence