Réaction #77476

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureunder reflux for 4 hours
3. 3
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
4. 4
   Lavagethe aqueous layer was washed with ethyl acetate
5. 5
   Extractionextracted with ethyl acetate
6. 6
   LavageThe organic layer was washed successively with water and saturated brine
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 1N hydrochloric acid (1 ml)
10. 10
    Concentrationconcentrated
11. 11
    AutreThe resultant crystal was recrystallized from ethanol-ethyl acetate

Mode opératoire

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.

Source