Benzoic acid, 2,4-dihydroxy-, hydrazide → 2,4-dihydroxy-N'-[1-[1-(4-iodophenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethyl]benzohydrazide

HRID 555594Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

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%).

Workup

temperatureAfter cooling
customevaporation of the solvent
customthe crude product was recrystallized from chloroform/ether

Sources & evidence

ORD record: ord-a07f681cb6cd42fc8154f68aadcbe617
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053453B2

Reaction notes

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