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

HRID 1611714Notes

Reaction equation

HRID 1611714 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.[CH2:12]([NH2:15])[CH2:13][NH2:14]>C(#N)C>[NH2:14][CH2:13][CH2:12][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

4

Reactant 2

HCID 3301EthylenediamineHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The starting material (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine is prepared in the following manner. A mixture of 2-amino-6-chloro-3-nitropyridine (65 g, 376 mmol), acetonitrile (400 ml), and ethylene diamine (500 ml) are stirred overnight (ca. 20 h) at 75–80° C. under argon. When the diamine is added, this reaction can become exothermic! The ethylene diamine is removed under reduced pressure, and then in vacuo (12 h). The completely dried material is suspended in 2M sodium hydroxide solution (500 ml) with vigorous stirring for 30 min. The solid is filtered. The yellow solid is suspended in water (500 ml) with vigorous stirring for 30 min., after which the solid is filtered. The water wash and filtration is repeated one more time to get rid of salts. The yellow solid is dried in vacuo. The crude yellow solid is triturated with ether (3×500 ml) and dried overnight in vacuo resulting in 59 g of 2-(2-aminoethyl)amino-6-amino-5-nitropyridine in >99% purity.

Workup

  1. customthis reaction
  2. customThe ethylene diamine is removed under reduced pressure
  3. customin vacuo (12 h)
  4. stirringwith vigorous stirring for 30 min
  5. filtrationThe solid is filtered
  6. stirringwith vigorous stirring for 30 min.
  7. filtrationafter which the solid is filtered
  8. washThe water wash
  9. filtrationfiltration
  10. customto get rid of salts
  11. customThe yellow solid is dried in vacuo
  12. customThe crude yellow solid is triturated with ether (3×500 ml)
  13. customdried overnight in vacuo
  14. customresulting in 59 g of 2-(2-aminoethyl)amino-6-amino-5-nitropyridine in >99% purity

Sources & evidence

ORD record
ord-e14ab689e5564dfca490eb650ddb4c7b
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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