Reaktion #77470

Reaktionsgleichung

water

7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

aminoguanidine hydrochloride

hydrochloric acid

→

7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Ausbeute 94.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 6 hours
3. 3
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in water
5. 5
   Waschenwashed with ethyl acetate
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe organic layer was washed successively with water and saturated brine
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    workup.DISSOLUTIONThe residue was dissolved in ethanol
11. 11
    Einengenconcentrated
12. 12
    Sonstigethe precipitated crystal was recrystallized from ethanol

Vorschrift

A solution of 7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.1 g) and aminoguanidine hydrochloride (0.54 g) in ethanol (30 ml) was combined with concentrated hydrochloric acid (1.0 ml) and water (1.0 ml) and heated under reflux for 6 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in water and 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 ethanol, combined with 1N hydrochloric acid (10 ml) and concentrated, and then the precipitated crystal was recrystallized from ethanol to obtain 7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound C) (1.4 g) as a colorless crystal.

Quelle