HCID 178492217, compound → N-(4-Methoxyphenyl)-4-methyl-1-phenyl-1H-pyrazol-3-amine

HRID 252643Notes

Reaction equation

HRID 252643 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:14]([CH3:15])[CH2:13][N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:14]([CH3:15])=[CH:13][N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 178492217HCID 178492217, compound

Product 1

HCID 21272310N-(4-Methoxyphenyl)-4-methyl-1-phenyl-1H-pyrazol-3-amine

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 200 ml round bottom flask, under nitrogen, was charged with N-(4-methoxyphenyl)-4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-amine (0.85 g, 3.02 mmol) and DCM (60.42 ml, 0.05 M). To this solution was added slowly manganese dioxide (0.58 g, 6.65 mmol). Reaction stirred at RT under a nitrogen atmosphere for 16 h. The reaction mixture was diluted with DCM and filtered over Celite®. The filtrate was concentrated to afford brown oil, which was purified by ISCO silica gel chromatography (20-40% EtOAc/hexanes) to afford N-(4-methoxyphenyl)-4-methyl-1-phenyl-1H-pyrazol-3-amine. MS m/z=280.2 [M+H]+. Calc'd for C17H17N3O: 279.34.

Workup

  1. customReaction
  2. filtrationfiltered over Celite®
  3. concentrationThe filtrate was concentrated
  4. customto afford brown oil, which
  5. customwas purified by ISCO silica gel chromatography (20-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-97f389432eb34a71961fb390a3278f2e
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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