3-[4-(4-Nitrophenoxy)phenyl]-1H-pyrazole-1-carboxamide → HCID 9817586, compound

HRID 2227718Notes

Reaction equation

HRID 2227718 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:19]=[CH:18][N:17]([C:20]([NH2:22])=[O:21])[N:16]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:19]=[CH:18][N:17]([C:20]([NH2:22])=[O:21])[N:16]=3)=[CH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 98186653-[4-(4-Nitrophenoxy)phenyl]-1H-pyrazole-1-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 9817586HCID 9817586, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[4-(4-nitrophenoxy)phenyl]-1H-pyrazole-1-carboxamide (100 mg, 0.308 mmol) in ethanol was flushed with nitrogen for 5 min, then palladium (10% on carbon, 20 mg) was added. The mixture was shaken under 40 psi of hydrogen for 16 hours. The mixture was then filtered through a bed of Celite and the solvent was removed in vacuo. The crude product was purified by column chromatography to give 57 mg (60%) of the title compound as a solid, mp 158-160° C. 1H NMR (CDCl3): δ8.22 (d, J=3.0 Hz, 1H), 7.75 (d, J=8.7 Hz, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.10 (bs, 1H), 6.90 (d, J=9.0 Hz, 2H), 6.70 (d, J=9.0 Hz, 2H), 6.66 (d, J=3.0 Hz, 1H), 5.25 (bs, 1H), 3.61 (bs, 2H).

Workup

  1. filtrationThe mixture was then filtered through a bed of Celite
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a5f591fca02f45ff8c8661789d23a60d
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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