3,4-Dichlorobenzaldehyde → 4-(3,4-Dichlorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dione

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Reaction Steps

3,4-Dichlorobenzaldehyde (0.17 g, 1.0 mmol), 1,3-cyclopentadione (0.1 g, 1.0 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.11 g, 1.0 mmol) were processed as described in Example 1 to provide 0.24 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.28 (t, 2H), 2.68 (m, 2H), 3.5 (s, 3H), 4.7 (s, 1H), 7.13 (dd, 1H), 7.33 (d, 1H), 7.49 (d, 1H), 9.58 (s, 1H), 10.45 (s, 1H); MS (ESI−) m/z 348 (M−H)−; Anal. calcd for C16H13N3Cl2O2: C, 54.71; H, 4.32; N, 11.26. Found: C, 54.37; H, 4.40; N, 10.80.

Provenance & Evidence