Reaktion #2438159

Reaktionsgleichung

1-(2-chlorophenyl)-2-methyl-5-(2-fluoro-phenyl)-1,3,5-pentanetrione

aniline

para-toluenesulfonic acid

→

2-(2-chlorophenyl)-6(2fluorophenyl)-3-methyl-1-phenyl-4(1H)-pyridinone

Ausbeute 25.1%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONXylene was distilled off from the reaction mixture and 300 ml of chloroform
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   SonstigeThe mixture obtained
4. 4
   Filtrationwas filtered
5. 5
   Waschenthe filtrate was washed first with 10% hydrochloric acid
6. 6
   WaschenAfter washing the chloroform phase further with water
7. 7
   Trocknenthe solution in chloroform was dried over anhydrous sodium sulfate
8. 8
   SonstigeSubsequent to removal of the sodium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    Sonstigethe residue was purified by column chromatography (eluent: ethyl acetate-n-hexane, 1:3)
11. 11
    Sonstigeto afford crude crystals
12. 12
    SonstigeThe crystals were recrystallized from ethyl acetate

Vorschrift

In 450 ml of xylene were suspended 15.3 g of 1-(2-chlorophenyl)-2-methyl-5-(2-fluoro-phenyl)-1,3,5-pentanetrione, 6.4 g of aniline, 6.6 g of para-toluenesulfonic acid and 85 g of Molecular Sieves 5A, followed by refluxing the resultant mixture for 8 hours. Xylene was distilled off from the reaction mixture and 300 ml of chloroform was added to the residue. The mixture obtained was filtered and the filtrate was washed first with 10% hydrochloric acid and then with a 10% aqueous solution of sodium hydroxide. After washing the chloroform phase further with water, the solution in chloroform was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate-n-hexane, 1:3) to afford crude crystals. The crystals were recrystallized from ethyl acetate, yielding 4.5 g of 2-(2-chlorophenyl)-6(2fluorophenyl)-3-methyl-1-phenyl-4(1H)-pyridinone having a melting point of 182°-183° C.

Quelle