1,3-Cyclohexanedione, 4,4-dimethyl- → 4-(4-bromo-3-chlorophenyl)-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dione

HRID 1837090Notes

Reaction equation

HRID 1837090 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[Cl:18].[CH3:19][C:20]1([CH3:28])[CH2:25][CH2:24][C:23](=O)[CH2:22][C:21]1=[O:27]>>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:22]3[C:21](=[O:27])[C:20]([CH3:28])([CH3:19])[CH2:25][CH2:24][C:23]=3[NH:1][C:2]3[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]2=3)=[CH:12][C:11]=1[Cl:18]

Participants

4

Reactant 3

HCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 140498064-Bromo-3-chlorobenzaldehyde

Product 1

HCID 102747394-(4-bromo-3-chlorophenyl)-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dioneYield 67.2%

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.08 g, 0.75 mmol), 3-chloro-4-bromobenzaldehyde (0.13 g, 0.75 mmol) from Example 40C, and 4,4-dimethyl-1,3-cyclohexanedione (0.10 g, 0.75 mmol) were processed as described in Example 22 to provide the title compound (0.22 g, 67%). 1H NMR (DMSO-d6) δ 0.92 (s, 3H), 0.98 (s, 3H), 1.78 (t, 2H), 2.55 (m, 2H), 3.47 (s, 3H), 4.81 (s, 1H), 7.0 (dd, 1H), 7.29 (d, 1H), 7.55 (d, 1H), 9.52 (bs, 1H), 9.67 (s, 1H); MS (ESI−) m/z 436 (M−H)−; Anal. Calcd for C19H19N3BrClO2: C, 52.23; H, 4.35; N, 9.62. Found: C, 52.35; H, 4.24; N, 9.62.

Sources & evidence

ORD record
ord-acb1de264a5845efb88be055db4d06c2
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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