1-(3'-Nitro-phenyl)-2-formylamino-propane → 1-(3'-Aminophenyl)-2-formylamino-propane

HRID 597733Notes

Reaction equation

HRID 597733 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([NH:13][CH:14]=[O:15])[CH3:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([NH:13][CH:14]=[O:15])[CH3:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 213274321-(3'-Nitro-phenyl)-2-formylamino-propane

Product 1

HCID 213274251-(3'-Aminophenyl)-2-formylamino-propane

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5.2 gm of 1-(3'-nitro-phenyl)-2-formylamino-propane was hydrogenated in methanol in the presence of Raney nickel at atmospheric pressure and room temperature. Thereafter, the catalyst was filtered off, the solvent was evaporated from the filtrate, and the residue was chromatographed on a silicagel column, using methanol/chloroform (2:8) as the flow agent. The eluate was evaporated, and the residue was recrystallized from ethyl acetate, yielding 1-(3'-aminophenyl)-2-formylamino-propane which had a melting point of 107° -108° C.

Workup

  1. filtrationThereafter, the catalyst was filtered off
  2. customthe solvent was evaporated from the filtrate
  3. customthe residue was chromatographed on a silicagel column
  4. customThe eluate was evaporated
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a17087da65784c37a316599519ad01b6
Source dataset
uspto-grants-1977_03
Patent number
US04015011

Reaction notes

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