Benzoic acid, 2-(4-nitrophenyl)hydrazide → N'-(4-Aminophenyl)benzohydrazide

HRID 437284Notes

Reaction equation

HRID 437284 reaction equation
[C:1]([NH:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[C:1]([NH:9][NH:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5185538Benzoic acid, 2-(4-nitrophenyl)hydrazideHCID 178418361HCID 178418361, compound

Product 1

HCID 20508846N'-(4-Aminophenyl)benzohydrazide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzoyl-2-(4-nitrophenyl)hydrazine (14.3 g, 0.056 mole) and 10% palladium/charcoal (catalytic amount) were suspended in ethanol (300 ml) in a Parr shaker bottle. The reaction mixture was hydrogenated at room temperature until hydrogen uptake ceased. The reaction mixture was filtered and the solvent was evaporated from the filtrate leaving a tan crystalline powder. Yield 11.5 g (90%), m.p. 134°-136° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated from the filtrate
  3. customleaving a tan crystalline powder

Sources & evidence

ORD record
ord-1872bf48b01641998f4f0a391c72dc8b
Source dataset
uspto-grants-1977_06
Patent number
US04030925

Reaction notes

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