Réaction #2305305

Équation de réaction

Acetic acid

3-(4-[5-chloro-3-(4-nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}-propionic acid ethyl ester

→

3-{4-[3-(4-Aminophenyl)-5-chloro-2-oxo-2H-pyridin-1-ylmethyl]phenyl}-propionic acid ethyl ester

Solvants

ethanol

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was then heated
2. 2
   Températureat reflux for 2 hours
3. 3
   FiltrationAfter basification with aqueous ammonia the mixture was filtered through a pad of celite (Diatomaceous Earth)
4. 4
   Autrethe filtrate evaporated to dryness
5. 5
   Lavagethe organic layer washed with brine
6. 6
   Séchagedried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated to dryness
9. 9
   AutreAfter purification by chromatography on silica gel with a gradient of 30-50% ethyl acetate in hexane the title compound
10. 10
    Autrewas obtained as an oil

Mode opératoire

Acetic acid (1 mL) followed by iron (160 mg, 2.9 mmol) were added to a solution of 3-(4-[5-chloro-3-(4-nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}-propionic acid ethyl ester (0.31 g, 0.72 mmol) in ethanol (10 mL) and water (5 mL) with stirring. The mixture was then heated at reflux for 2 hours and allowed to cool to room temperature. After basification with aqueous ammonia the mixture was filtered through a pad of celite (Diatomaceous Earth) and the filtrate evaporated to dryness. The residue was taken up in aqueous sodium bicarbonate/ethyl acetate and the organic layer washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. After purification by chromatography on silica gel with a gradient of 30-50% ethyl acetate in hexane the title compound was obtained as an oil.

Source