N,N-Dimethylethylenediamine → N~1~,N~1~-Dimethyl-N~2~-(3-nitropyridin-2-yl)ethane-1,2-diamine

HRID 1822104Notes

Reaction equation

HRID 1822104 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:11]([CH2:14][CH2:15][NH2:16])([CH3:13])[CH3:12]>C(O)C>[CH3:12][N:11]([CH3:13])[CH2:14][CH2:15][NH:16][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 15942982N~1~,N~1~-Dimethyl-N~2~-(3-nitropyridin-2-yl)ethane-1,2-diamineYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (1.76 g, 20.0 mmol) in ethanol is treated with Me2NCH2CH2NH2 (3.17 g, 20.0 mmol), stirred at ambient temperature for 17 h, heated to reflux temperature for 7 h, cooled to room temperature and concentrated in vacuo. The resulting solid residue is triturated with ethanol and suction filtered. The filtercake is air-dried to give the title compound as a yellow solid, 3.20 g (61% yield), mp 202-203° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 7 h
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid residue is triturated with ethanol and suction
  6. filtrationfiltered
  7. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-7cb05e95c4f14743b2fe46f209b8200d
Source dataset
uspto-grants-2009_10
Patent number
US07608717B2

Reaction notes

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