N,N-Dimethylethylenediamine → N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

HRID 1984534Notes

Reaction equation

HRID 1984534 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH2:15]>C(O)(C)C>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamineYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-fluoro-nitrobenzene (2.8 g, 20 mmol) and N,N-dimethylethylenediamine (3.3 mL, 30 mmol) in isopropanol is heated at 90°-100° C. for 16 h, cooled to 0° C. and filtered. The filtercake is washed with cold isopropanol and air-dried to give the title compound as an orange solid, 3.83 g (92% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperatureis heated at 90°-100° C. for 16 h
  2. filtrationfiltered
  3. washThe filtercake is washed with cold isopropanol
  4. customair-dried

Sources & evidence

ORD record
ord-c0cf241ae1fa491b81ac002ccfb9199a
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

Loading…