Cyanoacetamide → 5-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1980303Notes

Reaction equation

HRID 1980303 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[CH:17]N(C)C)[CH:15]=O)=[CH:10][CH:9]=1>[Na]>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:17]=[C:3]([C:1]#[N:2])[C:4](=[O:5])[NH:6][CH:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7898CyanoacetamideHCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

Product 1

HCID 27639105-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

Sodium (7 grams in 300 ml methanol) was stirred while a methanolic solution of 2-cyanoacetamide (16 grams) and 2-(4-chlorophenyl)-3-(dimethylamino)acrolein (37 grams) was added. The mixture was refluxed for 1 hour and the resulting precipitate was filtered, washed with ethanol, dissolved in hot water, and then acidified. The resulting precipitate was filtered, washed with water, and identified as the desired product, m.p. 278°-280° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 1 hour
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with ethanol
  5. dissolutiondissolved in hot water
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-b1d70592a55f4ed2902c8029af239b6e
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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