Ethylenediamine → SG 1842

HRID 463520Notes

Reaction equation

HRID 463520 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:12]([NH2:15])[CH2:13][NH2:14]>>[NH2:14][CH2:13][CH2:12][NH:15][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 69188Ethyl Nicotinate

Product 1

HCID 571799SG 1842

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl nicotinate (21.9 g.) and ethylenediamine (30 ml.) was heated to 100° C. for 16 hours under an atmosphere of argon. Excess ethylenediamine was removed by distillation in vacuo and the residue was dissolved in water (100 ml.) The insoluble material [bis(carboxamido)derivative] was removed by filtration. Evaporation of the filtrate, addition of toluene (50 ml.) followed by re-evaporation gave crude N-(2-aminoethyl)pyridine-3-carboxamide (26.5 g.) as its oily free base, essentially pure by TLC (SiO2 : 10% MeOH/CHCl3) and which was used without purification.

Workup

  1. customExcess ethylenediamine was removed by distillation in vacuo
  2. dissolutionthe residue was dissolved in water (100 ml.) The insoluble material [bis(carboxamido)derivative]
  3. customwas removed by filtration
  4. customEvaporation of the filtrate, addition of toluene (50 ml.)
  5. customfollowed by re-evaporation

Sources & evidence

ORD record
ord-f7aeb0481b594232b94315246dc8c05c
Source dataset
uspto-grants-1985_05
Patent number
US04520027

Reaction notes

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