4-Aminopyridine → HCID 22061296, compound

HRID 1829188Notes

Reaction equation

HRID 1829188 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([O:10][C:11](=O)[CH2:12][N+:13]#[C-:14])C.CN(C)C=[O:19]>>[N:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:11](=[O:10])[CH2:12][NH:13][C:14]2=[O:19])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 17274-AminopyridineHCID 6228DimethylformamideHCID 533707Ethyl isocyanoacetate

Product 1

HCID 22061296HCID 22061296, compound

Procedure

A mixture of 4-aminopyridine (25 g, 266 mmol) and ethylisocyanoacetate (35 g, 271 mmol) in N,N-dimethylformamide (250 ml) was heated under reflux for 90 minutes, and allowed to cool. The resulting precipitate was filtered off, and the filtrate heated under reflux for a further 5 hours. The cooled mixture was concentrated under reduced pressure, and the residue triturated with hot ethanol (500 ml). The resulting solid was filtered, and recrystallised from N,N-dimethylformamide to afford the title compound as a yellow crystalline solid, 47.8 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureto cool
  4. filtrationThe resulting precipitate was filtered off
  5. temperaturethe filtrate heated
  6. temperatureunder reflux for a further 5 hours
  7. concentrationThe cooled mixture was concentrated under reduced pressure
  8. customthe residue triturated with hot ethanol (500 ml)
  9. filtrationThe resulting solid was filtered
  10. customrecrystallised from N,N-dimethylformamide

Sources & evidence

ORD record
ord-6ac40638e53a426db887c585b42c3482
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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