Reaktion #1787712

Reaktionsgleichung

3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

aminoguanidine hydrochloride

hydrochloric acid

water

→

4-guanidinoimino-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride

Ausbeute 4.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 12 hours
2. 2
   SonstigeUnder reduced pressure, the solvent was evaporated
3. 3
   workup.ADDITIONTo the residue was added sodium hydrogen carbonate solution
4. 4
   Extraktionthe mixture was extracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water and saturated brine
6. 6
   Trocknendried with magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigethe residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N)
9. 9
   workup.DISSOLUTIONThe resulting oil was dissolved in ethanol
10. 10
    workup.ADDITIONto the solution was added 1N hydrochloric acid
11. 11
    SonstigeThe solvent was evaporated
12. 12
    Sonstigethe residue was recrystallized from ethanol-ethyl acetate

Vorschrift

A mixture of 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.70 g), aminoguanidine hydrochloride (0.34 g), concentrated hydrochloric acid (0.44 ml), water (0.44 ml) and ethanol (50 ml) was refluxed for 12 hours. Under reduced pressure, the solvent was evaporated. To the residue was added sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/MeOH/Et3N). The resulting oil was dissolved in ethanol, and to the solution was added 1N hydrochloric acid. The solvent was evaporated, and the residue was recrystallized from ethanol-ethyl acetate to give 4-guanidinoimino-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride (Compound 6) (0.04 g) as colorless crystals.

Quelle