4-Methylpyrazole → HCID 58128686, compound

HRID 2088462Notes

Reaction equation

HRID 2088462 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(=NO)C1C(=CC=CC=1)O>ClCCl.C(#N)C>[CH3:12][C:13]1[CH:14]=[N:15][N:16]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 34064-MethylpyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 1235464-Bromo-2-nitrotoluene

Product 1

HCID 58128686HCID 58128686, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. washThe filtrate was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d692ef81e2544abad346785ed265fe3
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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