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

HRID 1192240Notes

Reaction equation

HRID 1192240 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.CC(N)C(C)[NH2:14].[CH2:17]([N:19]([CH2:22]C)[CH2:20]C)[CH3:18].C(#N)C>O>[CH3:20][N:19]([CH3:22])[CH2:17][CH2:18][NH:14][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 1363622,3-Butanediamine

Product 1

HCID 3696952N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamineYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask, charged with 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), dimethylethane-1,2-diamine (0.55 g, 6.3 mmol), triethylamine (0.63 g, 6.3 mmol) and acetonitrile (10 mL). The resulting reaction mixture was stirred at ambient temperature for 9 hours. TLC analysis showed no acid remaining so the mixture was diluted with water and extracted with ethylacetate. The organic layer was separated and washed with brine and water, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography using a 95:5 mixture of dichloromethane and methanol as eluent to afford the title product as a brown solid (0.55 g, 42% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.91 (1H, m), 8.09 (2H, m), 6.62 (1H, m), 4.10 (1H, m), 3.50 (2H, m), 3.17 (2H, m), 2.21 (6H, s). MS m/z: 211.14 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethylacetate
  3. customThe organic layer was separated
  4. washwashed with brine and water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. additiona 95:5 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-ee90ca04f2c24698bb2e006d8f146ece
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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