N,N-Dimethylethylenediamine → N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamine

HRID 130663Notes

Reaction equation

HRID 130663 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N=[N+]=[N-])C.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20]>CC#N>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH:20][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 783082-Chloro-5-nitropyridineHCID 79118Ethane, azido-

Product 1

HCID 3696952N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine 106-A and EtN3 (4.7 g, 46.5 mmol) in CH3CN (150 ml) was added N,N-dimethylethlenediamine 106-B (4.1 g, 46.5 mmol). The solution was stirred at room temperature for 3 hours, extracted with EtOAc, washed (brine), dried(MgSO4) and concentrated to give N,N-dimethyl-N′-(5-nitropyridin-2-yl)ethane-1,2-diamine 106-C (5.2 g) as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washwashed (brine), dried(MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3632a75afb1e4d6bab2873d1474fea9c
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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