Dimethylformamide dimethyl acetal → 6-[2-(Dimethylamino)ethenyl]-5-propanoylpyridin-2(1H)-one

HRID 1649159Notes

Reaction equation

HRID 1649159 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10][CH3:11].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>CN(C)C=O>[CH3:15][N:16]([CH3:18])[CH:17]=[CH:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132320416-methyl-5-(n-propanoyl)-2(1H)-pyridinone

Product 1

HCID 537092406-[2-(Dimethylamino)ethenyl]-5-propanoylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 25 g of 6-methyl-5-(n-propanoyl)-2-(1H)-pyridinone, 200 ml of dimethylformamide and 25 ml of dimethylformamide dimethyl acetal was heated on a steam bath for 5 and 1/2 hours and the dimethylformamide was removed by heating the reaction mixture on a rotary evaporator. The residue was refluxed with 100 ml of ethanol, the mixture cooled, and the yellow solid was collected, washed with ethanol and dried in an oven at 90°-95° C. to yield 12.8 g of 6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone, m.p. 204°-206° C.

Workup

  1. temperaturewas heated on a steam bath for 5 and 1/2 hours
  2. customthe dimethylformamide was removed
  3. temperatureby heating the reaction mixture
  4. customon a rotary evaporator
  5. temperatureThe residue was refluxed with 100 ml of ethanol
  6. temperaturethe mixture cooled
  7. customthe yellow solid was collected
  8. washwashed with ethanol
  9. customdried in an oven at 90°-95° C.

Sources & evidence

ORD record
ord-60fe2ea270b640f8bb38362affdafe91
Source dataset
uspto-grants-1983_11
Patent number
US04415580

Reaction notes

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