Ammonium formate → Ethyl 1-(4-aminophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 8074Notes

Reaction equation

HRID 8074 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 2737215Ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 2808376Ethyl 1-(4-aminophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 1-(4-nitrophenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.5 g, 1.5 mmol) dissolved in methanol (4 mL) was added palladium on carbon and ammonium formate (0.428 g, 6.8 mmol). This mixture was stirred at room temperature overnight. The solvent was removed under vacuum, then the material was resuspended in chloroform, and washed with water (twice) and saturated sodium bicarbonate (once), and the organic layer dried over magnesium sulfate (MgSO4). The solid was filtered and the solvents removed under vacuum. The reaction product was purified over silica gel to yield the named product (m.p. 102° C.–103° C.).

Workup

  1. customThe solvent was removed under vacuum
  2. washwashed with water (twice) and saturated sodium bicarbonate (once), and the organic layer
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. filtrationThe solid was filtered
  5. customthe solvents removed under vacuum
  6. customThe reaction product was purified over silica gel

Sources & evidence

ORD record
ord-96385c6264c1424398d9348e12f7a5f7
Source dataset
uspto-grants-2006_08
Patent number
US07087634B2

Reaction notes

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