1-[2-(4-nitrophenyl)ethyl]-1H-pyrazole → HCID 43519590, compound

HRID 30688Notes

Reaction equation

HRID 30688 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 638109421-[2-(4-nitrophenyl)ethyl]-1H-pyrazole

Product 1

HCID 43519590HCID 43519590, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[2-(4-nitrophenyl)ethyl]-1H-pyrazole (0.8 g), 10% palladium carbon (80 mg) and ethanol (200 ml) was stirred under a hydrogen atmosphere at room temperature for 6 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate-hexane gave 1-[2-(4-aminophenyl)ethyl]-1H-pyrazole (520 mg, 75%) as colorless prism crystals. melting point: 73-74° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-eb8a67f084434f9794209b41c66634c3
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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