Methyl 4-(hydrazinecarbonyl)benzoate → HCID 178498000, compound

HRID 555606Notes

Reaction equation

HRID 555606 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([OH:14])=[C:12]([C:15](=O)[CH3:16])[C:11]([C:18]([F:21])([F:20])[F:19])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([NH:32][NH2:33])=[O:31])=[CH:28][CH:27]=1)=[O:25]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[C:15]([NH:33][NH:32][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:35][CH:34]=3)[CH3:16])[C:11]([C:18]([F:19])([F:20])[F:21])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 178466874HCID 178466874, compound

Product 1

HCID 178498000HCID 178498000, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1-(3,4-Dimethylphenyl)-5-hydroxy-3-trifluoromethyl-1H-pyrazol-4-yl)-ethanone (0.189 mmol, 56.5 mg) and 4-methoxycarbonylbenzhydrazide (0.189 mmol, 36.8 mg) were stirred in DMF at 100° C. for 2.2 hours and at 120° C. for 17 hours. After the solvent was removed by evaporation, the residue was resolved by silica gel thin layer chromatography (CHCl3/MeOH=10/1) to obtain 4-methoxycarbonylbenzoic N′-(1-(1-(3,4-dimethylphenyl)-3-trifluoromethyl-5-oxo-1,5-dihydropyrazol-4-ylidene)-ethyl)-hydrazide as a yellow solid (55.6 mg, 62%)

Workup

  1. customAfter the solvent was removed by evaporation

Sources & evidence

ORD record
ord-99b9f525b4df40c59d660076b30498b8
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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