NSC 378646 → 1,3-Dimethyl-N-phenyl-1H-pyrazole-4-carboxamide

HRID 2163523Notes

Reaction equation

HRID 2163523 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[CH3:7][N:6]1[CH:2]=[C:3]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[C:4]([CH3:8])=[N:5]1

Participants

5

Reactant 2

HCID 73028NSC 378646HCID 517045Sodium Acetate

Product 1

HCID 130317271,3-Dimethyl-N-phenyl-1H-pyrazole-4-carboxamideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-chloro-1,3-dimethyl-N-phenyl-4-pyrazolecarboxamide (2.7 g) was dissolved in ethanol (100 ml) and anhydrous sodium acetate (2 g) added. The mixture was hydrogenated at room temperature and 2 atmospheres pressure using palladium on carbon catalyst. On completion of the reaction, the catalyst was removed by filtration through celite and the filtrate evaporated in vacuo. Water (50 ml) was added and the product extracted with chloroform (3 × 25 ml). The combined extracts were washed with water, dried and evaporated. The product was crystallised from ethanol and 1,3-dimethyl-N-phenyl-4-pyrazolecarboxamide (2 g, 96%) was obtained as colourless needles, m.p. 91-92° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customOn completion of the reaction
  3. customthe catalyst was removed by filtration through celite
  4. customthe filtrate evaporated in vacuo
  5. additionWater (50 ml) was added
  6. extractionthe product extracted with chloroform (3 × 25 ml)
  7. washThe combined extracts were washed with water
  8. customdried
  9. customevaporated
  10. customThe product was crystallised from ethanol

Sources & evidence

ORD record
ord-a4c1f2f677254cfbadd2c1b512be0564
Source dataset
uspto-grants-1979_01
Patent number
US04134987

Reaction notes

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