2-(3,4-Dichlorophenyl)-2-oxoacetaldehyde → 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone

HRID 1881553Notes

Reaction equation

[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:7])[CH3:6].[Cl:8][C:9]1[CH:10]=[C:11]([C:16](=O)[CH:17]=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15]>C(O)(=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[N:2]([CH3:1])[N:3]=[C:4]([C:5](=[O:7])[CH3:6])[C:17]=2[OH:18])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Oxopropanal methylhydrazone (1.525 mmol, 152.7 mg) synthesized in Reference Synthetic Example 1 and (3,4-dichlorophenyl)(oxo)acetaldehyde (1.525 mmol, 310 mg) synthesized in Reference Synthetic Example 3 were dissolved in acetic acid (10 mL) and stirred at 110° C. for 1.5 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump, resolved by silica gel thin layer chromatography (n-hexane/AcOEt=3/2) and purified by silica gel thin layer chromatography (n-hexane/AcOEt=2/1) to give the desired product as a yellow solid (57.8 mg, yield 13%).

Workup

customsynthesized in Reference Synthetic Example 3
customThen, the solvent was evaporated
customthe residue was dried by means of a vacuum pump
custompurified by silica gel thin layer chromatography (n-hexane/AcOEt=2/1)

Sources & evidence

ORD record: ord-d1d416c39fd7478581e63aa9426a3dc4
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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