Potassium Carbonate → N'-(6-Oxo-1,6-dihydropyridin-2-yl)-N,N-dipropylformimidamide

HRID 1607087Notes

Reaction equation

HRID 1607087 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]=[N:10][CH2:11][CH2:12][CH3:13])[N:3]=1.[CH2:14](I)[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:13][CH2:12][CH2:11][N:10]([CH:9]=[N:8][C:4]1[NH:3][C:2](=[O:1])[CH:7]=[CH:6][CH:5]=1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178457528HCID 178457528, compound

Product 1

HCID 159470N'-(6-Oxo-1,6-dihydropyridin-2-yl)-N,N-dipropylformimidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.8 g (10 mmol) of N-(2-pyridon-6-yl)-N'-propylformamidine and N-(2-hydroxy-6-pyridyl)-N'-propylformamidine, 1.9 g (11 mmol) of propyl iodide and 1.5 g (11.mmol) of potassium carbonate are stirred at 80° for 24 hours in 30 ml of absolute ethanol. The reaction mixture is then filtered and concentrated by evaporation The residue is taken up in methylene chloride, washed with water and then dried over Na2SO4 and concentrated by evaporation. The resulting crude product is purified chromatographically. Crystallisation from methylene chloride/ether yields N-(2-pyridon-6-yl)-N',N'-di-n-propylformamidine and N-(2-hydroxy-6-pyridyl)-N',N'-di-n-propylformamidine having a melting point of 102°-104°.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated by evaporation The residue
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. customThe resulting crude product is purified chromatographically
  7. customCrystallisation from methylene chloride/ether

Sources & evidence

ORD record
ord-1ac1a6175d71461baf3138effbf546c5
Source dataset
uspto-grants-1989_09
Patent number
US04863938

Reaction notes

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