Water → N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

HRID 252629Notes

Reaction equation

HRID 252629 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)(O)[O-].[Na+].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20].O>C1COCC1>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-fluoronitrobenzene (2.0 g, 14 mmol) and sodium bicarbonate (5.9 g, 71 mmol) in 30 mL THF under nitrogen was added N1, N1-dimethylethane-1,2-diamine (1.7 mL, 16 mmol). The reaction was allowed to stir at ambient temperature for 3 h, and then a water-cooled reflux condenser was added and the mixture was heated to 70° C. for 16 h. The reaction was cooled to ambient temperature, filtered through paper, and concentrated in vacuo to give N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine as a yellow oil. This material was used without further purification.

Workup

  1. temperaturereflux condenser
  2. additionwas added
  3. temperaturethe mixture was heated to 70° C. for 16 h
  4. temperatureThe reaction was cooled to ambient temperature
  5. filtrationfiltered through paper
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a82a6cdc45e413db0bf0a8b5b741e26
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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