(3,4-Dimethylphenyl)(oxo)acetaldehyde → 1-[5-(3,4-dimethylphenyl)-1-methyl-4-hydroxy-1H-pyrazol-3-yl]ethanone

HRID 1881561Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Oxopropanal methylhydrazone (8.18 mmol, 819 mg) synthesized in Reference Synthetic Example 1 and (3,4-dimethylphenyl)(oxo)acetaldehyde (7.57 mmol, 1.227 g) synthesized in Reference Synthetic Example 5 were dissolved in acetic acid (30 mL) and stirred at 100° C. for about 5 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump and subjected to silica gel column chromatography (n-hexane/AcOEt=2/1, and 4/1) to give the crude product. The crude product was stirred with CHCl3/n-hexane for a while, and then recovered by filtration. The filtered solid was combined with a solid obtained by silica gel thin layer chromatography purification (n-hexane/AcOEt=4/1) of the filtrate to give the desired product as an orange solid (237.5 mg, yield 13%).

Workup

customsynthesized in Reference Synthetic Example 5
customThen, the solvent was evaporated
customthe residue was dried by means of a vacuum pump
customto give the crude product
filtrationrecovered by filtration
customobtained by silica gel thin layer chromatography purification (n-hexane/AcOEt=4/1) of the filtrate

Sources & evidence

ORD record: ord-75fd6305df5744d18c0555e743606842
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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