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

HRID 2297111Notes

Reaction equation

HRID 2297111 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-a838b32e5a844a2bb22bc7e64501a337
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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