2,4-dihydroxybenzohydrazide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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%). After the solvent was removed by evaporation the residue was dried with a vacuum pump filtered with chloroform the filtrate was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 mg (0.2 mmol) of the 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-carbaldehyde synthesized in 1) and 34 mg (0.20 mmol) of 2,4-dihydroxybenzoic hydrazide were stirred in 1 ml of ethanol at room temperature for 96 hours. The precipitated solid was collected by filtration and washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively to obtain 53 mg of the desired product (yield 70%). The precipitated solid was collected by filtration washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 mg (0.2 mmol) of the 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-carbaldehyde synthesized in 1) and 34 mg (0.20 mmol) of 2,4-dihydroxybenzoic hydrazide were stirred in 1 ml of ethanol at room temperature for 96 hours. The precipitated solid was collected by filtration and washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively to obtain 53 mg of the desired product (yield 70%). The precipitated solid was collected by filtration washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.03 g (3 mmol) of 1-(5-hydroxy-1-(4-iodophenyl)-3-methyl-1H-pyrazol-4-yl)-ethanone and 505 mg (3 mmol) of 2,4-dihydroxybenzoic hydrazide were dissolved in 50 ml of DMSO and heated at 85° C. for 9 hours with stirring. After cooling and evaporation of the solvent, the crude product was recrystallized from chloroform/ether to give 1.39 g of the desired product as a pale brown solid (yield 94%). After cooling evaporation of the solvent the crude product was recrystallized from chloroform/ether

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.03 g (3 mmol) of 1-(5-hydroxy-1-(4-iodophenyl)-3-methyl-1H-pyrazol-4-yl)-ethanone and 505 mg (3 mmol) of 2,4-dihydroxybenzoic hydrazide were dissolved in 50 ml of DMSO and heated at 85° C. for 9 hours with stirring. After cooling and evaporation of the solvent, the crude product was recrystallized from chloroform/ether to give 1.39 g of the desired product as a pale brown solid (yield 94%). After cooling evaporation of the solvent the crude product was recrystallized from chloroform/ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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%). After the solvent was removed by evaporation the residue was dried with a vacuum pump filtered with chloroform the filtrate was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 mg (0.2 mmol) of the 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-carbaldehyde synthesized in 1) and 34 mg (0.20 mmol) of 2,4-dihydroxybenzoic hydrazide were stirred in 1 ml of ethanol at room temperature for 96 hours. The precipitated solid was collected by filtration and washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively to obtain 53 mg of the desired product (yield 70%). The precipitated solid was collected by filtration washed with 1 ml of ethanol, 1 ml of ether and 1 ml of methanol successively

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.03 g (3 mmol) of 1-(5-hydroxy-1-(4-iodophenyl)-3-methyl-1H-pyrazol-4-yl)-ethanone and 505 mg (3 mmol) of 2,4-dihydroxybenzoic hydrazide were dissolved in 50 ml of DMSO and heated at 85° C. for 9 hours with stirring. After cooling and evaporation of the solvent, the crude product was recrystallized from chloroform/ether to give 1.39 g of the desired product as a pale brown solid (yield 94%). After cooling evaporation of the solvent the crude product was recrystallized from chloroform/ether