N,N-di-n-propylformamide dimethyl acetal → N'-(6-Oxo-1,6-dihydropyridin-2-yl)-N,N-dipropylformimidamide

HRID 1607084Notes

Reaction equation

HRID 1607084 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.CO[CH:11](OC)[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]>C1(C)C(C)=CC=CC=1>[CH3:15][CH2:14][CH2:13][N:12]([CH:11]=[N:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][CH:3]=1)[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 13161383N,N-di-n-propylformamide dimethyl acetalHCID 1785076342-Amino-6-hydroxypyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

8.3 g (76 mmol) of 6-amino-2-hydroxypyridine and 20 g (114 mmol) of N,N-di-n-propylformamide dimethyl acetal are placed in 70 ml of xylene under argon. .The whole is heated at 100° for 1/2 hour while stirring It is then allowed to cool, is concentrated by evaporation under a water-jet vacuum and the residue is filtered over 10 times the amount of Florisil using methylene chloride. The fractions containing the product are concentrated by evaporation and then crystallised from n-hexane. N-(2-hydroxy-6-pyridyl)-N',N'-di-n-propylformamidine and N-(2-pyridon-6-yl)-N',N'-di-n-propylformamidine having a melting point of 102°-104° are obtained.

Workup

  1. temperature.The whole is heated at 100° for 1/2 hour
  2. temperatureto cool
  3. concentrationis concentrated by evaporation under a water-jet vacuum
  4. filtrationthe residue is filtered over 10 times the amount of Florisil
  5. additionThe fractions containing the product
  6. concentrationare concentrated by evaporation
  7. customcrystallised from n-hexane

Sources & evidence

ORD record
ord-fd7a7eb8db224cc7bdf922ccf3cbcdec
Source dataset
uspto-grants-1989_09
Patent number
US04863938

Reaction notes

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