5-Methyl-2-(3-methyl-4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-one → 2-(4-Amino-3-methylphenyl)-5-methyl-1,2-dihydro-3H-pyrazol-3-one

HRID 722225Notes

Reaction equation

HRID 722225 reaction equation
[H][H].[CH3:3][C:4]1[NH:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=2)[C:6](=[O:19])[CH:5]=1>[Pd].O1CCCC1>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([N:7]2[C:6](=[O:19])[CH:5]=[C:4]([CH3:3])[NH:8]2)=[CH:10][C:11]=1[CH3:18]

Participants

5

Reactant 2

HCID 218838945-Methyl-2-(3-methyl-4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 218838762-(4-Amino-3-methylphenyl)-5-methyl-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogen was introduced under atmospheric pressure into the mixture of 350 mg of 5-methyl-2-(3-methyl-4-nitrophenyl)-1,2-dihydropyrazol-3-one, 70 mg of Pd/C and 50 ml of tetrahydrofuran until the theoretical uptake. Afterwards, the catalyst was filtered off with suction and the mixture was concentrated to dryness under reduced pressure and the residue was stirred in t-butyl methyl ether. The solid was filtered off with suction and dried under reduced pressure.

Workup

  1. filtrationAfterwards, the catalyst was filtered off with suction
  2. concentrationthe mixture was concentrated to dryness under reduced pressure
  3. filtrationThe solid was filtered off with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-92788c62c87442159c8485c81f7ecd9b
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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