Ethanol → 3-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-(2-pyridyl)hydrazone

HRID 839212Notes

Reaction equation

HRID 839212 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][CH:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[NH2:23].C(O)C>C(O)(=O)C.O>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:22][N:23]=[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][CH:17]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 786452-HydrazinopyridineHCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 543686393-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-(2-pyridyl)hydrazoneYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

Stir an admixture of 2 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde, 0.92 g of 2-hydrazinopyridine, 50 ml of ethanol and 2 drops of glacial acetic acid for 36 hours at room temperature. Cool the admixture and then form a precipitate with 50 ml of water to obtain a 95% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-(2-pyridyl)hydrazone [m.p. 228° to 231° C (with decomposition) from dimethylformamide/water].

Workup

  1. temperatureCool the admixture

Sources & evidence

ORD record
ord-f01a48f9ede241c6b0ef0e314e119ed4
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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