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

HRID 1995599Notes

Reaction equation

HRID 1995599 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-c6b2332ba88b47e79c436acebb218273
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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