Hydrazine → N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

HRID 1984535Notes

Reaction equation

HRID 1984535 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.NN.[O-]S([O-])(=O)=O.[Mg+2]>CO.[Ni]>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

Product 1

HCID 522698N-[2-(dimethylamino)ethyl]benzene-1,2-diamineYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of N,N-dimethyl-N′-(2-nitrophenyl)ethane-1,2-diamine (3.83 g, 18.3 mmol) and Raney-Nickel (0.5 g) in methanol is treated dropwise with hydrazine (5 mL), stirred at room temperature until reaction is complete by TLC, treated with Celite and MgSO4 and filtered. The filtercake is washed with methanol. The combined filtrate is concentrated in vacuo to give the title compound as a brown oil, 3.11 g (94% yield), identified by HPLC and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. washThe filtercake is washed with methanol
  3. concentrationThe combined filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-4c87b64c6dfa457bb35b2ed95ed1bf3b
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

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