Ethylenediamine → 6-[(2-Aminoethyl)amino]pyridine-3-carbonitrile

HRID 2375305Notes

Reaction equation

HRID 2375305 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH2:10]([NH2:13])[CH2:11][NH2:12]>>[NH2:12][CH2:11][CH2:10][NH:13][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 113694056-[(2-Aminoethyl)amino]pyridine-3-carbonitrileYield 77%

Conditions

Temperature
50 °C

Procedure

To 100 mL of ethylene diamine at 50° C. under nitrogen was added 2-chloro-5-cyanopyridine (10 g, 0.0722 mol) in small portions over a period of 3 h. The reaction mixture was stirred at 50° C. for an additional 5 h. The reaction mixture was concentrated to near dryness under reduced pressure and the crude residue obtained was purified by chromatography using chloroform/methanol (9/1) as eluent to afford 9 g of the title compound as a solid (77%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude residue obtained
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-cd8b0385e8064ee88f635a755780740f
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

Loading…