3-Aminopyridine → 3-(Pyridin-3-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione

HRID 2097319Notes

Reaction equation

HRID 2097319 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([O:10][C:11]1[C:12](=O)[C:13](=[O:18])[C:14]=1[O:15]CC)[CH3:9]>CCO>[CH2:8]([O:10][C:11]1[C:14](=[O:15])[C:13](=[O:18])[C:12]=1[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH3:9]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 123228Diethyl squarate

Product 1

HCID 105129913-(Pyridin-3-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminopyridine (12.3 g, 130 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (21.5 g; 125 mmol) in 130 mL EtOH. The mixture was heated to reflux for 16 h, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (7% EtOH in EtOAc) to give the title compound as a yellow powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (7% EtOH in EtOAc)

Sources & evidence

ORD record
ord-b70e2df2d6df42369de4d07b5ad090bd
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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