Ethylenediamine → 2,6-Diamino-N2-(2-aminoethyl)-5-nitropyridine

HRID 1823522Notes

Reaction equation

HRID 1823522 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH2:12][CH2:13][CH2:14][NH2:15].[OH-].[Na+]>O>[NH2:12][CH2:13][CH2:14][NH:15][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 221423802,6-Diamino-N2-(2-aminoethyl)-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 mmol of 2-amino-6-chloro-3-nitropyridine and 15 mmol of 1,2-diaminoethane were stirred at reflux for fourteen hours. The reaction mixture was concentrated in vacuo and solution of 1.5 mmol of NaOH in water was added. This solution was extracted twice with 95%/5% methylene chloride/methanol. The aqueous was then saturated with salt and extracted twice with 95%/5% acetonitrile/methanol and then finally extracted twice with 95%/5% ethylacetate/methanol. All organic fractions were combined and dried over sodium sulfate to obtain (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine.

Workup

  1. temperatureat reflux for fourteen hours
  2. additionwas added
  3. extractionThis solution was extracted twice with 95%/5% methylene chloride/methanol
  4. extractionsaturated with salt and extracted twice with 95%/5% acetonitrile/methanol
  5. extractionfinally extracted twice with 95%/5% ethylacetate/methanol
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-d3852f758efe4f95b571521d1f02ff4f
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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