Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)- → Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

HRID 2285585Notes

Reaction equation

HRID 2285585 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH:11][CH:12]=[O:13])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][NH:11][CH:12]=[O:13])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 5008489Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-

Product 1

HCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-Yield 81.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 1,600 ml of ethanol, 30 g of 2-(4-nitrophenyl)-1-formylhydrazine was catalytically reduced at room temperature, using palladium-carbon as a catalyst. The reaction mixture was filtered and the filtrate was evaporated to dryness, whereby 20.5 g of white solid 2-(4-aminophenyl)-1-formylhydrazine was obtained. Melting point: 123° to 125° C.

Workup

  1. customwas catalytically reduced at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-492ae1755ce34bd7b6473490bef01514
Source dataset
uspto-grants-1982_04
Patent number
US04323643

Reaction notes

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