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

HRID 2228597Notes

Reaction equation

HRID 2228597 reaction equation
Cl[C:2]1N=[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:16](#N)C>>[NH2:14][CH2:13][CH2:12][NH:15][C:2]1[CH:8]=[C:6]([CH3:16])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6342Acetonitrile2×HCID 184699642-Chloro-4-methyl-5-nitropyrimidine

Product 1

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

Procedure

2-Chloro-4-methyl-5-nitropyrimidine (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-7936208f04e84b9db4d7fad817585762
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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