Reaktion #320009

Reaktionsgleichung

2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine

trifluoroacetic acid

sodium hydroxide

3-mercaptopropionic acid

→

title compound

Ausbeute 52.4%

11-(2-Carboxyethylthio)-2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

Ausbeute 52.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred under ice cooling for 2 hours
2. 2
   workup.ADDITIONwas added the mixture
3. 3
   Extraktionthe aqueous layer was extracted with 200 ml of methylene chloride
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Sonstigethe residue obtained
7. 7
   Sonstigeby removing the solvent under reduced pressure
8. 8
   Sonstigewas recrystallized from ethyl acetate

Vorschrift

While stirring under ice cooling, 1 g of 2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine was added to a mixed solution of 8 ml of trifluoroacetic acid and 6 ml of methylene chloride, then 0.25 g of 3-mercaptopropionic acid was added to the solution and the mixture was stirred under ice cooling for 2 hours. After completion of the reaction, 180 ml of ice water was added the mixture, the mixture was adjusted to about pH 3 with a 1N-sodium hydroxide aqueous solution and then the aqueous layer was extracted with 200 ml of methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate and the residue obtained by removing the solvent under reduced pressure was recrystallized from ethyl acetate to obtain 0.63 g of the title compound as white powder.

Quelle