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

HRID 1837055Notes

Reaction equation

HRID 1837055 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]1[C:18](=O)[CH2:17][C:15](=[O:16])[CH2:14]1.[NH2:20][C:21]1[N:25]([CH3:26])[NH:24][C:23](=[O:27])[CH:22]=1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:22]3[C:23](=[O:27])[NH:24][N:25]([CH3:26])[C:21]=3[NH:20][C:18]3[CH2:13][CH2:14][C:15](=[O:16])[C:17]2=3)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 855054-Chloro-3-nitrobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 102699304-(4-Chloro-3-nitrophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 55.4%

Procedure

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.

Sources & evidence

ORD record
ord-de09aa47d73a4648944412149981dc02
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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