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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1837089Generated: October 26, 2026

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

https://huagongshe.com/reaction/1837089

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-CyclopentanedioneHCID 77466—
Reactant5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 252198—
Reactant4-Bromo-3-chlorobenzaldehydeHCID 14049806—
Product4-(4-Bromo-3-chlorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneHCID 1029405667.6%

Reaction Steps

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.84 g, 0.75 mmol), 4-bromo-3-chlorobenzaldehyde (0.157 g, 0.75 mmol) from Example 40C, and 1,3-cyclopentanedione (0.074 g, 0.75 mmol) was processed as described in Example I to provide 0.20 g of the title compound. 1H NMR (DMSO-d6) δ 2.29 (t, 2H), 2.68 (m, 2H), 3.49 (s, 3H), 4.69 (s, 1H), 7.02 (dd, 1H), 7.33 (d, 1H), 7.6 (d, 1H), 9.55 (s, 1H), 10.41 (s,1H); MS (ESI−) m/z 394 (M−H)−;

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06780872B2
Source datasetuspto-grants-2004_08
ORD IDord-e09c8f34c0b947599191ea1d1e2ca73e
Source noteuspto-grants-2004_08