Hydrochloric Acid → 1-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride

HRID 437301Notes

Reaction equation

HRID 437301 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[H][H]>C(O)C.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31065344-Chlorobenzoic N2-(4-nitrophenyl)hydrazideHCID 178418361HCID 178418361, compound

Product 1

HCID 214278261-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(4-Chlorobenzoyl)-2-(4-nitrophenyl)hydrazine (2.92g, 0.01 mole) and 5% palladium on barium sulfate (catalytic amount) were suspended in a mixture of ethanol (350 ml) and concentrated hydrochloric acid (5 ml) in a Parr shaker bottle. The reaction mixture was hydrogenated at room temperature until the theoretical amount of hydrogen had been taken up. The reaction mixture was filtered and the solvent was evaporated from the filtrate leaving a tan solid. Yield 2.9 g (99%), m.p. 209° C (dec.).

Workup

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

Sources & evidence

ORD record
ord-2dd5157278a94b48bff83f32f717e6e3
Source dataset
uspto-grants-1977_06
Patent number
US04030925

Reaction notes

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