Methyl 4-(hydrazinecarbonyl)benzoate → HCID 178497997, compound

HRID 555618Notes

Reaction equation

HRID 555618 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[C:4]([CH3:17])[C:3]=1[C:18](=O)[CH3:19].[CH3:21][O:22][C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=1)=[O:24]>CN(C=O)C>[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[C:4]([CH3:17])[C:3]=1[C:18](=[N:32][NH:31][C:29]([C:28]1[CH:33]=[CH:34][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:26][CH:27]=1)=[O:30])[CH3:19]

Participants

4

Reactant 2

HCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 178466982HCID 178466982, compound

Product 1

HCID 178497997HCID 178497997, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.2 mmol of 1-{5-hydroxy-3-methyl-1-[5-(trifluoromethyl)-2-pyridinyl]-1H-pyrazol-4-yl}ethanone and 0.2 mmol of 4-methoxycarbonylbenzhydrazide were heated in 2 ml of DMF at 100° C. for 9 hours with stirring. After the solvent was removed by evaporation, the resulting crude product was dissolved in chloroform and recrystallized from hexane to obtain 66 mg of the desired product, methyl 4-{([2-(1-{5-hydroxy-3-methyl-1-[5-(trifluoromethyl)-2-pyridinyl]-1H-pyrazol-4-yl}ethylidene)hydrazino]carbonyl}benzoate (yield 72%).

Workup

  1. customAfter the solvent was removed by evaporation
  2. dissolutionthe resulting crude product was dissolved in chloroform
  3. customrecrystallized from hexane

Sources & evidence

ORD record
ord-cc67cf336743461f8994e4670a0cc47c
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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