Acetic Acid → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 839202Notes

Reaction equation

CO[C:3]([NH:5][N:6]=[C:7]([C:9]1[O:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)[CH3:8])=O.[C:17]1(NN)C=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:25](O)(=[O:27])C.[CH2:29](O)C>>[N+:14]([C:11]1[O:10][C:9]([C:7]2[C:8]([CH:25]=[O:27])=[CH:29][N:5]([C:3]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:6]=2)=[CH:13][CH:12]=1)([O-:16])=[O:15]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 702Ethanol

HCID 7516Phenylhydrazine

HCID 71394061Methyl 2-[1-(5-nitrofuran-2-yl)ethylidene]hydrazine-1-carboxylate

Product 1

HCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Procedure

boiling 5-nitro-2-acetylfuran-methoxycarbonylhydrazone with 1.5 moles of phenylhydrazine and 0.1 mole of glacial acetic acid in ethanol for 3 hours under reflux.

Workup

customfor 3 hours
temperatureunder reflux

Sources & evidence

ORD record: ord-fb704dfd600c47efbf6bbcfecac16ede
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04093812

Reaction notes

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