Hydrazinecarboxylic acid, ethyl ester → 3-(5-Nitro-2-furyl)-1-(2-pyridyl)pyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone

HRID 839235Notes

Reaction equation

HRID 839235 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:22]([O:24][C:25](=[O:28])[NH:26][NH2:27])[CH3:23]>C(O)(=O)C.C(O)C>[CH2:22]([O:24][C:25]([NH:26][N:27]=[CH:14][C:13]1[C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:12]=1)=[O:28])[CH3:23]

Participants

5

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 203261643-(5-Nitrofuran-2-yl)-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 538806453-(5-Nitro-2-furyl)-1-(2-pyridyl)pyrazole-4-carboxaldehyde-ethoxycarbonylhydrazoneYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

Heat 0.6 g of 3-(5-nitro-2-furyl)-1-(2-pyridyl)pyrazole-4-carboxaldehyde together with 0.27 g of ethylcarbazate and 2 drops of glacial acetic acid in 8 ml of ethanol for 1.5 hours at boiling point. Cool the resulting product for a 97% yield of 3-(5-nitro-2-furyl)-1-(2-pyridyl)pyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone [m.p. 215° to 216° C (with decomposition) from toluene].

Sources & evidence

ORD record
ord-87e1316c0710435b8c2e2b1c6bf262e9
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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