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

HRID 1733564Notes

Reaction equation

HRID 1733564 reaction equation
C[O-].[Na+].[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[CH:20]N(C)C)[CH:18]=O)=[CH:13][CH:12]=1>CO>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:20]=[C:6]([C:4]#[N:5])[C:7](=[O:8])[NH:9][CH:18]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehydeHCID 10942334Sodium Methoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 37.6 g. of sodium methoxide in 650 ml. of methanol is added 29.24 g. of cyanoacetamide followed by 26.1 g. of 2-(4-chlorophenyl)-3-(dimethylamino)-2-propenal. The resulting solution is heated at reflux temperature for 16 hours to separate a yellow solid. Then 50 ml. of glacial acetic acid is added and the mixture is diluted with water, causing a new yellow solid to separate. This solid is collected by filtration and is washed with water to give 60.5 g. of the product of the Example m.p. 285°-290° C.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux temperature for 16 hours
  3. customto separate a yellow solid
  4. additionof glacial acetic acid is added
  5. additionthe mixture is diluted with water
  6. customto separate
  7. filtrationThis solid is collected by filtration
  8. washis washed with water
  9. customto give 60.5 g

Sources & evidence

ORD record
ord-b767003a589d47f48e2bf82c744e8901
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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