Dimethylformamide dimethyl acetal → 2(1H)-Pyridinone, 5-acetyl-6-[2-(dimethylamino)ethenyl]-

HRID 1649158Notes

Reaction equation

HRID 1649158 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:11])[NH:8][C:9]=1[CH:10]=[CH:14][N:15]([CH3:17])[CH3:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 44217365-acetyl-6-methyl-2(1H)-pyridinone

Product 1

HCID 37350622(1H)-Pyridinone, 5-acetyl-6-[2-(dimethylamino)ethenyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 15.1 g of 5-acetyl-6-methyl-2(1H)-pyridinone, 200 ml of dimethylformamide and 15 ml of dimethylformamide dimethyl acetal was stirred at room temperature for 30 minutes, heated gently with stirring on a steam bath for 2 hours, then allowed to cool and stirred at room temperature overnight. The golden yellow needles that separated were collected, washed with methanol and dried in a vacuum oven at 80° C. to yield 10.7 g of 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone, m.p. 238°-240° C.

Workup

  1. temperatureheated gently
  2. stirringwith stirring on a steam bath for 2 hours
  3. temperatureto cool
  4. stirringstirred at room temperature overnight
  5. customThe golden yellow needles that separated
  6. customwere collected
  7. washwashed with methanol
  8. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-db5f0b18b7da4ed7a95b820eca5fd0d7
Source dataset
uspto-grants-1983_11
Patent number
US04415580

Reaction notes

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