Methylhydrazine → HCID 22493241, compound

HRID 1816296Notes

Reaction equation

HRID 1816296 reaction equation
[CH3:1][N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])=O.[CH3:17][NH:18]N>C(O)C>[CH3:17][N:18]1[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[CH:4][CH:3]=[N:2]1.[CH3:1][N:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[N:18]1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 292656HCID 292656, compound

Product 2

HCID 22493241HCID 22493241, compoundHCID 224932491-Methyl-3-(2-nitrophenyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Dimethylamino)-2′-nitroacrylophenone (3.0 g, 13.5 mmol) in absolute ethanol (25 mL) was treated with methylhydrazine (800 μL, 20 mmol) and heated to reflux for 5 hours. The solvent was distilled off, and the residue chromatographed on silica eluting with 2:1 hexane:ethyl acetate to provide 1-methyl-5-(2-nitrophenyl)pyrazole (1.9 g) and 1-methyl-3-(2-nitrophenyl)pyrazole (350 mg).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. distillationThe solvent was distilled off
  4. customthe residue chromatographed on silica eluting with 2:1 hexane

Sources & evidence

ORD record
ord-0d9a425be9134d0893782c655ba9adfe
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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