1,3-Cyclopentanedione → HCID 10199630, compound

Participants

Reaction Steps

3-Bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), 1,3-cyclopentadione (0.15 g, 1.5 mmol), and 5-amino-2-methyl-1,2-dihydropyrazol-3-one (0.17 g, 1.5 mmol), prepared by the method of (C. Taylor and J. Barton, J.Am.ChemSoc., (1959) 81, 2448) were processed as described in Example 1 to provide 0.32 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.21 (t, 2H), 2.59 (m, 2H), 3.38 (s, 3H), 4.75 (s, 1H), 7.13 (m, 1H), 7.2 (t, 1H), 7.42 (dd, 1H), 10.16 (s, 1H), 10.51 (bs, 1H); MS (ESI−) m/z 378 (M−H)−; Anal. Calcd for C16H13N3BrFO2: C, 50.21; H, 3.56; N, 10.98. Found: C, 50.76; H, 4.09; N, 10.52.

Provenance & Evidence