(Phenylmethyl)hydrazine → 5-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-one

HRID 1078352Notes

Reaction equation

HRID 1078352 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([CH2:8][C:9]([O:11]CC)=O)=O.[CH2:19]([NH:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[NH:27][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9](=[O:11])[CH2:8]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 229023385-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-oneYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.6 g of ethyl 3,4-dimethoxybenzoylacetate were suspended in ethanol, and 3.5 g of benzylhydrazine were added dropwise with ice cooling over the course of 1.5 hours. The reaction mixture was stirred at room temperature for 12 hours. Then the precipitated product was filtered out and washed first with ethanol and then with tert-butyl methyl ether. 4.36 g of 5-(3,4-dimethoxyphenyl)-2-benzylpyrazolin-3-one were obtained. Melting point: 164°-166° C.

Workup

  1. filtrationThen the precipitated product was filtered out
  2. washwashed first with ethanol

Sources & evidence

ORD record
ord-fc46fa4d3c0f4fe499a3f0143a3f0d1d
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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