Hydroxyamine hydrochloride → N-{[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydroxylamine

HRID 839208Notes

Reaction equation

HRID 839208 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[N+:9]([C:12]1[O:16][C:15]([C:17]2[C:21]([CH:22]=O)=[CH:20][N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:18]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]>CN(C)C=O>[N+:9]([C:12]1[O:16][C:15]([C:17]2[C:21]([CH:22]=[N:7][OH:8])=[CH:20][N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:18]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 54343732N-{[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydroxylamineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add (while stirring) 7.61 g of sodium acetate and 6.58 g of hydroxylamine hydrochloride to 25.0 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde in 75 ml of dimethylformamide, the temperature rising slightly. Stir for a further 45 minutes at from 30° to 35° C and for one hour at room temperature. Clafify with degased active charcoal and then pour the solution onto 1 kg of ice and water. Vacuum filter and wash with water to obtain 98% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehydeoxime [m.p. 199° to 201° C with decomposition (from toluene)].

Workup

  1. customClafify with degased active charcoal
  2. additionpour the solution onto 1 kg of ice and water
  3. filtrationVacuum filter
  4. washwash with water

Sources & evidence

ORD record
ord-5521072044234600993709f492513c43
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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