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

HRID 1837061Notes

Reaction equation

HRID 1837061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[CH2:11]1[C:16](=O)[CH2:15][C:13](=[O:14])[CH2:12]1.[NH2:18][C:19]1[N:23]([CH3:24])[NH:22][C:21](=[O:25])[CH:20]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:20]3[C:21](=[O:25])[NH:22][N:23]([CH3:24])[C:19]=3[NH:18][C:16]3[CH2:11][CH2:12][C:13](=[O:14])[C:15]2=3)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 99029934-(3,4-Dichlorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 68.5%

Procedure

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.

Sources & evidence

ORD record
ord-e0ca9ad02e404c568db9780cb52a61d8
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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