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

HRID 1489652Notes

Reaction equation

HRID 1489652 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-10bc736b0dea4b95a4742425c2fce2df
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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