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

HRID 722224Notes

Reaction equation

HRID 722224 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][NH2:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:13](OC)(=[O:18])[CH2:14][C:15]([CH3:17])=O>C1(C)C=CC=CC=1>[CH3:17][C:15]1[NH:12][N:11]([C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=2)[C:13](=[O:18])[CH:14]=1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 13158578(3-Methyl-4-nitrophenyl)hydrazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 500 mg of 3-methyl-4-nitrophenylhydrazine, 0.32 ml of methyl acetoacetate and 20 ml of toluene was heated to 100° C. for 8 hours. After cooling, the reaction mixture was concentrated 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. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. filtrationThe solid was filtered off with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1d7534c20f0a472882f3e77a1f4f46aa
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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