Methyl 4-(hydrazinecarbonyl)benzoate → HCID 178498006, compound

HRID 555617Notes

Reaction equation

HRID 555617 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[C:12]([OH:13])=[C:11]([C:14](=O)[CH3:15])[C:10]([CH3:17])=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([NH:28][NH2:29])=[O:27])=[CH:24][CH:23]=1)=[O:21]>CS(C)=O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([NH:29][NH:28][C:26]([C:25]3[CH:30]=[CH:31][C:22]([C:20]([O:19][CH3:18])=[O:21])=[CH:23][CH:24]=3)=[O:27])[CH3:15])[C:10]([CH3:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 178466983HCID 178466983, compound

Product 1

HCID 178498006HCID 178498006, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

0.2 mmol of 1-[1-(6-chloro-3-pyridazinyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]ethanone and 0.2 mmol of 4-methoxycarbonylbenzhydrazide were dissolved in 2 ml of DMSO and heated at 100° C. for 8 hours with stirring. After the solvent was removed by evaporation, the crude product was dissolved in chloroform and recrystallized from ether to obtain 55 mg of the desired product, methyl 4-[(2-{1-[1-(6-chloro-3-pyridazinyl)-3-methyl-5-oxo-1,5-dihydropyrazol-4-ylidene]-ethyl}hydrazino)carbonyl]benzoate (yield 64%).

Workup

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

Sources & evidence

ORD record
ord-f4979609c5a84da79bf1aaf9d8d8119c
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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