3,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester → 1-(3-Aminophenyl)-3,5-dimethyl-1h-pyrazole-4-carboxylic acid ethyl ester

HRID 8064

Reaction equation

HRID 8064 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6569693,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 98138381-(3-Aminophenyl)-3,5-dimethyl-1h-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound of Example 2 (1.8 g) was dissolved in ethanol then 0.2 g 5% Pd/C was added to the solution. The mixture was treated with hydrogen gas at 45 psi. Upon completion of the reaction, the solution was filtered through Celite, and the filtrate concentrated under vacuum. The named product slowly crystallized upon standing (m.p. 93° C.–95° C.).

Workup

  1. customUpon completion of the reaction
  2. filtrationthe solution was filtered through Celite
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe named product slowly crystallized

Sources & evidence

ORD record
ord-7fc1f7aaa5b34943a693ad3861040cc8
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Linked notes

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