Benzoic acid, 2,4-dihydroxy-, hydrazide → HCID 178465644, compound

HRID 555605Notes

Reaction equation

HRID 555605 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].[OH:22][C:23]1[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:24]=1[C:25]([NH:27][NH2:28])=[O:26]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[C:15]([NH:28][NH:27][C:25](=[O:26])[C:24]3[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:23]=3[OH:22])[CH3:16])[C:11]([C:18]([F:20])([F:21])[F:19])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 166785Benzoic acid, 2,4-dihydroxy-, hydrazideHCID 178466874HCID 178466874, compound

Product 1

HCID 178465644HCID 178465644, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(1-(3,4-Dimethylphenyl)-5-hydroxy-3-trifluoromethyl-1H-pyrazol-4-yl)-ethanone (0.173 mmol, 51.5 mg) and 2,4-dihydroxybenzoic hydrazide (0.173 mmol, 30.6 mg) were stirred in ethanol (5 ml) at 80° C. for 19 hours. After the solvent was removed by evaporation, the residue was dried with a vacuum pump and filtered with chloroform, and the filtrate was concentrated and resolved by silica gel thin layer chromatography (CHCl3/MeOH=10/1) to obtain 2,4-dihydroxybenzoic N′-(1-(1-(3,4-dimethylphenyl)-3-trifluoromethyl-5-oxo-1,5-dihydropyrazol-4-ylidene)-ethyl)-hydrazide as a pale yellow solid (67 mg, yield 87%, purity 80.7%).

Workup

  1. customAfter the solvent was removed by evaporation
  2. customthe residue was dried with a vacuum pump
  3. filtrationfiltered with chloroform
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-81dead320869443491ea549bf80bd10f
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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