1-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole → 1-(3,4-dimethylphenyl)-1H-pyrazol-3-amine

HRID 2409831Notes

Reaction equation

HRID 2409831 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]>CO.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 665875041-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole

Product 1

HCID 283012451-(3,4-dimethylphenyl)-1H-pyrazol-3-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of 1-(3,4-dimethylphenyl)-3-nitro-1H-pyrazole (900 mg, 4.15 mmol, 1.00 equiv) in methanol/ethyl acetate (20/10 mL). The solution was treated with Pd/C (500 mg) and stirred under an atmosphere of hydrogen overnight at room temperature. The reaction progress was monitored by LCMS. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 750 mg (97%) of 1-(3,4-dimethylphenyl)-1H-pyrazol-3-amine as a yellow solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0ebfb1ba27e444d796a049035d156184
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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