Ethanol → 3,5-dimethyl-1-(2-aminophenyl)-1H-Pyrazole-4-carboxylic acid ethyl ester

HRID 8062

Reaction equation

HRID 8062 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]=[CH:14][C:13]=2[N+:18]([O-])=O)[C:10]=1[CH3:11])=[O:5])[CH3:2].C(O)C.[H][H]>[Pd].C(OCC)(=O)C>[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]=[CH:14][C:13]=2[NH2:18])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 99657643,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 98998923,5-dimethyl-1-(2-aminophenyl)-1H-Pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.4 g) in a solution of equal proportions of ethanol and ethyl acetate was added 5% Pd/C (37 mg). The solution was treated with hydrogen gas at 45 psi. Upon completion of the reaction, the mixture was filtered through Celite, then the filtrate concentrated under vacuum. The named product was collected as an oil, which then was purified by flash chromatography to provide a solid product having a melting point of 59° C.–61° C.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe named product was collected as an oil, which
  5. customthen was purified by flash chromatography
  6. customto provide a solid product

Sources & evidence

ORD record
ord-ed62a267b1e1458b8a6848506377f05d
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Linked notes

Loading…