ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylate → ethyl 4-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazole-3-carboxylate

HRID 639975Notes

Reaction equation

HRID 639975 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:24])[CH2:10][N:11]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:12]2)[CH:5]=[CH:6][CH:7]=1>[Pd].CO.ClCCl>[NH2:16][C:14]1[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:12][N:11]([CH2:10][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[O:24])[CH:15]=1

Participants

5

Reactant 1

HCID 68638240ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylate

Product 1

HCID 68637919ethyl 4-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazole-3-carboxylateYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxylate (0.168 g, 0.5 mmol) was hydrogenated over 10% palladium on carbon (0.034 g) in a mixture of methanol (6 ml) and dichloromethane (3 ml) for 3 hours. The mixture was filtered through Celite and the filtrate was evaporated to leave ethyl 4-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazole-3-carboxylate (0.135 g, 88% yield):

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b346c981c03a43e79240dd573ce6575a
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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