Reaktion #455579

Reaktionsgleichung

ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

ethyl 2,3,4,5-tetrafluorobenzoylacetate

2-amino-6-(t-butylamino)-3,5-difluoropyridine

aminoacrylate

→

title compound

ethyl 1-[6-(t-butylamino)-3,5-difluoropyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction by TLC
2. 2
   EinengenThe solution was concentrated under reduced pressure
3. 3
   workup.ADDITIONTo the residue were added 0.6 g of anhydrous potassium carbonate and 1 ml of N,N-dimethylformamide
4. 4
   Temperaturto cool
5. 5
   SonstigeThe solution was separated
6. 6
   workup.ADDITIONby adding 30 ml of chloroform and 300 ml of distilled water
7. 7
   Waschenthe chloroform layer was washed twice with 300 ml of distilled water
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    FiltrationThe precipitate was collected by filtration
11. 11
    Waschenwashed with ethanol and diisopropylether successively

Vorschrift

To 1 ml chloroform solution of ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate prepared from 0.27 g of ethyl 2,3,4,5-tetrafluorobenzoylacetate by normal process was added 2-amino-6-(t-butylamino)-3,5-difluoropyridine until completion of the conversion into the aminoacrylate form was confirmed by monitoring the reaction by TLC. The solution was concentrated under reduced pressure. To the residue were added 0.6 g of anhydrous potassium carbonate and 1 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 15 minutes and allowed to cool. The solution was separated by adding 30 ml of chloroform and 300 ml of distilled water, and the chloroform layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and allowed to stand. The precipitate was collected by filtration, washed with ethanol and diisopropylether successively to obtain 0.15 g of the title compound as a colorless powder.

Quelle