Methyl 4-(hydrazinecarbonyl)benzoate → HCID 178498001, compound

HRID 555597Notes

Reaction equation

HRID 555597 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[C:14]([C:17](=O)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:32][NH:31][C:29](=[O:30])[C:28]3[CH:27]=[CH:26][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:34][CH:33]=3)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 178466979HCID 178466979, compound

Product 1

HCID 178498001HCID 178498001, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

30.5 mg (0.11 mmol) of 1-(1-(4-tert-butylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-ethanone and 23.1 mg (0.11 mmol) of 4-methoxycarbonylbenzhydrazide were dissolved in 3.0 ml of DMF and stirred at 100° C. for 3 hours. After cooling and evaporation of the solvent, the crude product was recrystallized from ethyl acetate/n-hexane to give 32.9 mg of the desired product as a yellow solid (yield 66%).

Workup

  1. temperatureAfter cooling
  2. customevaporation of the solvent
  3. customthe crude product was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-cf9e18a3c0714bb5b2306785ecf31387
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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