Reaktion #77476

Reaktionsgleichung

water

7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

aminoguanidine hydrochloride

hydrochloric acid

→

7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 4 hours
3. 3
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
4. 4
   Waschenthe aqueous layer was washed with ethyl acetate
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed successively with water and saturated brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 1N hydrochloric acid (1 ml)
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe resultant crystal was recrystallized from ethanol-ethyl acetate

Vorschrift

A solution of 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one in ethanol (10 ml) was combined with aminoguanidine hydrochloride (0.041 g), concentrated hydrochloric acid (0.078 ml) and water (0.078 ml), and the mixture was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and the aqueous layer was washed with ethyl acetate. The aqueous layer was made alkaline with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid (1 ml) and concentrated. The resultant crystal was recrystallized from ethanol-ethyl acetate to obtain 7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound G) (0.05 g) as a colorless crystal.

Quelle