Ethylenediamine → (2-Aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine

HRID 31750Notes

Reaction equation

HRID 31750 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]([NH2:15])[CH2:13][NH2:14]>C(#N)C>[NH2:14][CH2:13][CH2:12][NH:15][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 22142401(2-Aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Chloro-4-methyl-5-nitropyridine (2.0 g, 11.5 mmol) in acetonitrile (10 ml) was added dropwise to ethylenediamine (2.5 ml) in acetonitrile (10 ml). The mixture was stirred overnight at room temperature. The solvent was removed by rotary evaporation and the residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide. The aqueous layer was further extracted 4 times with dichloromethane. The combined organic layers were washed with a saturated sodium chloride solution, dried and concentrated in vacuo to give (2-aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine as an orange solid (1.74 g).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide
  3. extractionThe aqueous layer was further extracted 4 times with dichloromethane
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fda66a26239646cbb517a662171c1af7
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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