HCID 178522146, compound → HCID 178508056, compound

HRID 20286Notes

Reaction equation

HRID 20286 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]([N+:16]([O-])=O)=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:15]([NH2:16])=[CH:14][NH:13][N:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178522146HCID 178522146, compound

Product 1

HCID 178508056HCID 178508056, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Nitro-1H-pyrazole-3-carboxylic acid (4-fluorophenyl)-amide (15 g) was dissolved in 200 ml of ethanol, treated with 1.5 g of 10% palladium on carbon under a nitrogen atmosphere, then hydrogenated at room temperature and pressure overnight. The catalyst was removed by filtration through Celite and the filtrate evaporated. The crude product was dissolved in acetone/water (100 ml:100 ml) and after slow evaporation of the acetone the product was collected by filtration as a brown crystalline solid (8.1 g). (LC/MS: Rt 1.58, [M+H]+ 220.95).

Workup

  1. customhydrogenated at room temperature
  2. custompressure overnight
  3. customThe catalyst was removed by filtration through Celite
  4. customthe filtrate evaporated
  5. dissolutionThe crude product was dissolved in acetone/water (100 ml:100 ml)
  6. customafter slow evaporation of the acetone the product
  7. filtrationwas collected by filtration as a brown crystalline solid (8.1 g)

Sources & evidence

ORD record
ord-d6f6040a89ac41aba91090055d17fceb
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Reaction notes

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