3,4-Dichlorobenzaldehyde → HCID 10271803, compound

HRID 1862429Notes

Reaction equation

HRID 1862429 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH:13]=O.[CH3:19][C:20]1([CH3:28])[CH2:25][CH2:24][C:23](=O)[CH2:22][C:21]1=[O:27]>>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]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:15]=[CH:16][C:17]=1[Cl:18]

Participants

4

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 10271803HCID 10271803, compoundYield 68%

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.08 g, 0.75 mmol), 3,4 dichlorobenzaldehyde (0.13 g, 0.75 mmol), and 4,4-dimethyl-1,3-cyclohexanedione (0.10 g, 0.75 mmol) were processed as described in Example 22 to provide 0.2 g (67%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 0.99 (s, 3H), 1.78 (t, 2H), 2.65 (m, 2H), 3.45 (s, 3H), 4.83 (s, 1H), 7.08 (dd, 1H), 7.29 (d, 1H), 7.42 (d, 1H), 9.52 (s, 1H), 9.68 (s, 1H); MS (ESI−) m/z 390 (M−H)−; Anal. calcd for C19H19N3Cl2O2: C, 58.16;H, 4.84; N, 10.71. Found: C, 58.23;H, 4.75; N, 10.68.

Sources & evidence

ORD record
ord-aa130c1fc4604c10a7a141194c09b2ea
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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