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

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Reaction Steps

4-Chloro-3-nitrobenzaldehyde (0.27 g, 1.5 mmol), 1,3-cyclopentadione (0.15 g, 1.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.17 g, 1.5 mmol) were processed as described in Example 1 to provide 0.3 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.3 (t, 2H), 2.68 (m, 2H), 3.5 (s, 3H), 4.81 (s, 1H), 7.48 (dd, 1H), 7.6 (d, 1H), 7.78 (d, 1H), 9.61 (bs, 1H), 10.49 (s, 1H); MS (ESI−) m/z 359 (M−H)−; Anal. calcd for C16H13N4ClO4: C, 53.27; H, 3.63; N, 15.53. Found: C, 53.16; H, 3.88; N, 14.83.

Provenance & Evidence