1-benzyl-3-methyl-4-nitroso-5-phenyl-1H-pyrazole → 1-Benzyl-3-methyl-5-phenyl-1H-pyrazol-4-amine

HRID 719290Notes

Reaction equation

HRID 719290 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([N:19]=O)[C:10]([CH3:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CCOC(C)=O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:11]([NH2:19])[C:10]([CH3:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 218979641-benzyl-3-methyl-4-nitroso-5-phenyl-1H-pyrazole

Product 1

HCID 461679331-Benzyl-3-methyl-5-phenyl-1H-pyrazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 2.32 g of 1-phenyl-butane-1,2,3-trione 2-oxime in 31 mL of EtOH was added a suspension of 2.43 g benzyl hydrazine dihydrochloride in 9 mL EtOH. The reaction mixture was warmed to rt and stirred for 96 h. The reaction mixture was concentrated under reduced pressure and purified by means of MPLC (120 g SiO2, 45% EtOAc:Heptane) to obtain 1-benzyl-3-methyl-4-nitroso-5-phenyl-1H-pyrazole. A suspension of 2.55 g 1-benzyl-3-methyl-4-nitroso-5-phenyl-1H-pyrazole, 34 mL EtOAc and 500 mg 10% Pd/C was reacted under 40 psi H2 atmosphere using a Parr apparatus. After 4 h, the suspension was filtered through Celite (EtOH eluting) and the filtrate was concentrated under reduced pressure and purified by means of MPLC (120 g SiO2, 60% EtOAc:Heptane) to give the title compound as an orange oil.

Workup

  1. customwas reacted under 40 psi H2 atmosphere
  2. filtrationthe suspension was filtered through Celite (EtOH eluting)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by means of MPLC (120 g SiO2, 60% EtOAc:Heptane)

Sources & evidence

ORD record
ord-ae6fb9c1b6574153add934b304c46c38
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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