N-(2-nitrophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine → N-(2-aminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine

HRID 373058Notes

Reaction equation

HRID 373058 reaction equation
[CH2:1]([O:3][C:4]([N:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])=[O:5])[CH3:2]>CO.[Pd]>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 19811333N-(2-nitrophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine

Product 1

HCID 19811357N-(2-aminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamineYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-ethoxycarbonyl-N-(2-nitrophenyl)-N',N'-dimethylethylenediamine (1.08 g) in methanol (25 ml) was added 10% palladium-on-carbon (0.1 g). The mixture was stirred under a hydrogen atmosphere at atmospheric pressure for 30 minutes, and filtered. The solvent was distilled off under reduced pressure to give 0.93 g of N-(2-aminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine.

Workup

  1. filtrationfiltered
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-198ae35e9f884dcb9b879511ef85a533
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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