Dimethylformamide dimethyl acetal → 5-Acetyl-1,2-dihyro-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile

HRID 462709Notes

Reaction equation

HRID 462709 reaction equation
C(C1C=C(C#N)C(=O)NC=1[CH:10]=[CH:11][N:12]([CH3:14])[CH3:13])(=O)C.[C:18]([C:21]1[CH:22]=[C:23]([C:29]#[N:30])[C:24](=[O:28])[NH:25][C:26]=1C)(=[O:20])[CH3:19].COC(OC)N(C)C>CO>[C:18]([C:21]1[CH:22]=[C:23]([C:29]#[N:30])[C:24](=[O:28])[N:25]([CH:10]=[CH:11][N:12]([CH3:14])[CH3:13])[CH:26]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrileHCID 53841137HCID 53841137, compound

Product 1

HCID 704997985-Acetyl-1,2-dihyro-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

D-3. 5-Acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile--A mixture containing 35.2 g of 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile, 300 ml of methanol and 30 ml of dimethylformamide dimethyl acetal was heated with stirring on a steam bath for 4 and 1/2 hours and then allowed to cool to room temperature. The precipitated yellow solid was collected, washed with methanol and dried in an oven under reduced pressure at 95° C. to yield 16.4 g of 5-acetyl-1,2-dihyro-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile, m.p. 267°-270° C.

Workup

  1. temperaturewas heated
  2. customThe precipitated yellow solid was collected
  3. washwashed with methanol
  4. customdried in an oven under reduced pressure at 95° C.

Sources & evidence

ORD record
ord-fcf7b4ea92c14a3c923a7cfa7930f736
Source dataset
uspto-grants-1985_05
Patent number
US04517190

Reaction notes

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