Reaktion #1756562

Reaktionsgleichung

4-hydroxy-3-[3-(3-carboxyphenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone

N-hydroxysuccinimide

dicyclohexylcarbodiimide

methanol

→

4-hydroxy-3-[3-[3-[(2-hydroxyethyl)aminocarbonyl]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone

Ausbeute 34.3%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationInsolubles were filtered
2. 2
   workup.ADDITION0.33 ml of ethanolamine was added to the filtrate
3. 3
   workup.STIRRINGthis was stirred at room temperature for 2.5 hours
4. 4
   SonstigeTo the residue obtained by concentration under reduced pressure
5. 5
   Temperaturthis was heated
6. 6
   Temperaturunder reflux
7. 7
   TemperaturAfter ice-cooling
8. 8
   Filtrationcrystals were filtered
9. 9
   Waschenwashed with methanol
10. 10
    Sonstigedried

Vorschrift

To a mixed solution of 1.57 g of 4-hydroxy-3-[3-(3-carboxyphenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone, 50 ml of dimethylformamide and 0.58 g of N-hydroxysuccinimide was added a solution of 1.03 g of dicyclohexylcarbodiimide in 5 ml of dimethylformamide, and this was stirred at room temperature overnight. Insolubles were filtered, 0.33 ml of ethanolamine was added to the filtrate, and this was stirred at room temperature for 2.5 hours. To the residue obtained by concentration under reduced pressure was added 30 ml of methanol, and this was heated under reflux. After ice-cooling, crystals were filtered, washed with methanol, and dried to obtain 0.61 g of 4-hydroxy-3-[3-[3-[(2-hydroxyethyl)aminocarbonyl]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (96a)] as a yellow crystal.

Quelle