Reaktion #1668

ord-506fcc7b31c241b1b92a78d6c6e2a5ef

Reaktionsgleichung

CC(=O)O
acetic acid
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

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe resulting suspension was refluxed overnight
  2. 2
    SonstigeDuring this time a yellow solid was formed
  3. 3
    FiltrationThe resulting yellow orange solid was filtered off
  4. 4
    Waschenwashed several times with water
  5. 5
    Sonstigedried

Vorschrift

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 acid (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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726176uspto-grants-1998_03