Ethyl Acetate → 2-phenyl-2H-pyrazole-3,4-diamine

HRID 1693504Notes

Reaction equation

HRID 1693504 reaction equation
[N:1]([C:3]1[CH:7]=[N:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]=1[NH2:14])=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>CCO>[C:8]1([N:5]2[C:4]([NH2:14])=[C:3]([NH2:1])[CH:7]=[N:6]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 107501065-Amino-4-nitroso-1-phenylpyrazole

Product 1

HCID 106548192-phenyl-2H-pyrazole-3,4-diamineYield 27.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-nitroso-2-phenyl-2H-pyrazol-3-ylamine (100 mg, 0.53 mmol) in EtOH (1 mL) is added SnCl3-2H2O (240 mg, 1.06 mmol). The mixture is then heated to 60° C. for 30 min. After cooling down the mixture, it is poured into a mixture of EtOAc (20 mL) and saturated aqueous NaHCO3 solution (20 mL). The solid is removed by filtration through Celite. The filtrate is put into separatory funnel to collect the organic layer, which is washed with brine and dried over MgSO4. After filtering off the drying agent, the filtrate is concentrated to provide the crude 2-phenyl-2H-pyrazole-3,4-diamine (˜25 mg) and used immediately for next step.

Workup

  1. additionis added SnCl3-2H2O (240 mg, 1.06 mmol)
  2. temperatureAfter cooling down the mixture, it
  3. customThe solid is removed by filtration through Celite
  4. customThe filtrate is put into separatory funnel
  5. customto collect the organic layer, which
  6. washis washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtering off the drying agent
  9. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-d81e0ae429fe4de896cd1a5f10364049
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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