Hydrazine → tert-Butyl 2-[(2-Aminophenyl)amino]ethylcarbamate

HRID 1984538Notes

Reaction equation

HRID 1984538 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O)([CH3:4])([CH3:3])[CH3:2].NN.[O-]S([O-])(=O)=O.[Mg+2]>CO.[Ni]>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 47453724tert-Butyl 2-(2-nitrophenylamino)ethylcarbamate

Product 1

HCID 28875325tert-Butyl 2-[(2-Aminophenyl)amino]ethylcarbamateYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of [2-(2-nitrophenylamino)ethyl]carbamic acid t-butyl ester (6 g, 21.3 mmol) and Raney-Nickel (0.5 g) in methanol is treated dropwise with hydrazine (0.8 mL, 25 mmol), stirred at room temperature until reaction is complete by TLC, treated with Celite and MgSO4 and filtered. The filtercake is washed with methanol. The filtrates are combined and concentrated in vacuo to give the title compound as a brown oil, 3.85 g (72% yield), identified by HPLC and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. washThe filtercake is washed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a578f7ac6d2c41a4aacfa81cfa3169ba
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

Loading…