2-Nitrophenylurethane → 2-[(Ethoxycarbonyl)amino]aniline

HRID 275421Notes

Reaction equation

HRID 275421 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)=[O:5])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 2479042-Nitrophenylurethane

Product 1

HCID 122150062-[(Ethoxycarbonyl)amino]anilineYield 64.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

The solution of N-(ethoxycarbonyl)-2-nitroaniline (2.0 g, 9.5 mmol) in absolute ethanol (25 mL) was hydrogenated at atmospheric pressure in the presence of 10% palladium hydroxide/carbon catalyst (200 mg). The catalyst was filtered off using a celite pad and the filtrate was evaporated. The residue was crystallized from isopropyl ether to give 2-[(ethoxycarbonyl)amino]aniline as a colorless solid (820 mg, 64.6% ).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-df2c2bbefcdb41cf88d94d53c715ce70
Source dataset
uspto-grants-1995_02
Patent number
US05393771

Reaction notes

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