Reacción #2214

ord-3a2c011f1b3e4de5a080b95b7446e37f

Ecuación de reacción

CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12
acetic
CN(C)C=C(C=O)c1ccc(Cl)cc1
2-(4-chlorophenyl)-3-dimethylaminopropenal
C[O-].[Na+]
sodium methoxide
N#CCC(N)=O
cyanoacetamide
N#Cc1cc(-c2ccc(Cl)cc2)c[nH]c1=O
3-cyano-5-(4-chlorophenyl)-2-pyridinone

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe resulting suspension was refluxed overnight
  2. 2
    OtroDuring this time a yellow solid was formed
  3. 3
    workup.ADDITIONwas added
  4. 4
    FiltraciónThe resulting yellow orange solid was filtered off
  5. 5
    Lavadowashed several times with water
  6. 6
    Otrodried

Procedimiento

To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic add (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728698uspto-grants-1998_03