1-(2,4-Difluorophenyl)-N-ethyl-4-nitroso-1H-pyrazol-5-amine → 1-(2,4-difluorophenyl)-N5-ethyl-1H-pyrazole-4,5-diamine

HRID 383569Notes

Reaction equation

HRID 383569 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[C:12]([N:17]=O)[CH:11]=[N:10]1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][CH3:16])=[C:12]([NH2:17])[CH:11]=[N:10]1

Participants

5

Reactant 2

HCID 866529991-(2,4-Difluorophenyl)-N-ethyl-4-nitroso-1H-pyrazol-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 671975031-(2,4-difluorophenyl)-N5-ethyl-1H-pyrazole-4,5-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(2,4-difluorophenyl)-N-ethyl-4-nitroso-1H-pyrazol-5-amine (1.21 g, 5 mmol) in 20 mL of MeOH was hydrogenated for 3 h with hydrogen gas in a balloon in the presence of palladium (200 mg of the 10% wt. on activated carbon). The reaction mixture was filtered through a pad of celite washing with MeOH. The solvent was removed on the rotovap affording 1-(2,4-difluorophenyl)-N5-ethyl-1H-pyrazole-4,5-diamine as a bright orange viscous oil. This material was used without purification. MS (ES+): 224.1 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with MeOH
  3. customThe solvent was removed on the rotovap

Sources & evidence

ORD record
ord-801cfcf22a4e456cb444b34ad40c37f1
Source dataset
uspto-grants-2013_02
Patent number
US08367671B2

Reaction notes

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