Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Methylpyrazole | HCID 3406 | — |
| Reactant | Salicylaldehyde oxime | HCID 7200 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-2-nitrotoluene | HCID 123546 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58128686 | HCID 58128686 | 60% |
Reaction Steps
A dried flask under nitrogen was charged with 4-bromo-1-methyl-2-nitro-benzene (40 mmol), 4-methylpyrazole (20 mmol), Cs2CO3 (13 g), Cu2O (290 mg, 2 mmol), salicylaldoxime (1.1 g, 8 mmol) and 12 mL of acetonitrile. The mixture was heated at 80° C. for 24 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane and filtered through celite. The filtrate was washed with water, dried and concentrated under reduced pressure. Column chromatography on silica gel (DCM/Hexane 30-100%) gave 4-methyl-1-(4-Methyl-3-nitro-phenyl)-1H-pyrazole as a yellow solid (60% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08435990B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-2d692ef81e2544abad346785ed265fe3 |
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| Source note | uspto-grants-2013_05 |
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