Dimethylformamide dimethyl acetal → 1,2-Dihydro-6-(2-dimethylaminoethenyl)-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile

HRID 1649161Notes

Reaction equation

HRID 1649161 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[C:11](=[O:14])[CH2:12][CH3:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[C:11](=[O:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132320386-Methyl-2-oxo-5-propanoyl-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 540674681,2-Dihydro-6-(2-dimethylaminoethenyl)-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 9.5 g of 1,2-dihydro-6-methyl-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile, 50 ml of dimethylformamide and 8 ml of dimethylformamide dimethyl acetal was stirred at room temperature overnight and then concentrated to dryness on a rotary evaporator. The residue was refluxed with isopropyl alcohol; the insoluble yellow solid was collected, washed with isopropyl alcohol and dried at 90° C. to yield 2.8 g of 1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile, m.p. 278°-280° C. with decomposition. The mother liquor was treated with decolorizing charcoal, filtered and concentrated to about 150 ml and allowed to stand at room temperature. The product that separated was collected, washed with isopropyl alcohol and dried to yield another 1.8 g of product, m.p. 270° C.

Workup

  1. concentrationconcentrated to dryness on a rotary evaporator
  2. temperatureThe residue was refluxed with isopropyl alcohol
  3. customthe insoluble yellow solid was collected
  4. washwashed with isopropyl alcohol
  5. customdried at 90° C.

Sources & evidence

ORD record
ord-d55feac1216f4c64b870bcbb0e9c5c5b
Source dataset
uspto-grants-1983_11
Patent number
US04415580

Reaction notes

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