Methane → 2-(1H-pyrazol-1-yl)aniline

HRID 2198761Notes

Reaction equation

HRID 2198761 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)([O-])=O.C.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

6

Reactant 3

HCID 297MethaneHCID 6050161-(2-Nitrophenyl)-1H-pyrazoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 27797102-(1H-pyrazol-1-yl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a Parr hydrogenation apparatus is successively added 20 g. (0.106 M.) of 1-(o-nitrophenyl)-pyrazole and 150 ml. of methanol and the resultant solution is hydrogenated in the presence of 1.0 g. of hydrogenation catalyst (10% Pd on active charcoal) at between 40 and 50 p.s.i. of hydrogen pressure at room temperature. After the theoretical uptake of hydrogen is achieved, the reaction mixture is filtered to remove the palladium and the solvent is removed on a rotary evaporator. Ether is then added to the resultant mixture and after removing the precipitated solids by filtration, the solvent is evaporated to yield a light amber colored oil (Yield: 90%).

Workup

  1. customat room temperature
  2. filtrationthe reaction mixture is filtered
  3. customto remove the palladium
  4. customthe solvent is removed on a rotary evaporator
  5. additionEther is then added to the resultant mixture
  6. customafter removing the precipitated solids
  7. filtrationby filtration
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-4b1bac9c52464d0389322ae5252885cb
Source dataset
uspto-grants-1982_11
Patent number
US04359474

Reaction notes

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