Reaktion #1787914

Reaktionsgleichung

7-(2-chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one

aminoguanidine hydrochloride

hydrochloric acid

water

→

7-(2-chlorophenyl)-4-(4-chlorophenyl)-5-guanidinoimino-5,6,7,8-tetrahydrocinnoline hydrochloride

Ausbeute 115.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 6 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
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified with silica gel column chromatography (ethyl acetate-methanol)
8. 8
   workup.DISSOLUTIONThe resulting crystals were dissolved in 1N hydrochloric acid (1 ml)
9. 9
   Einengenthe solution was concentrated
10. 10
    SonstigeThe residue was recrystallized from ethanol-ethyl acetate

Vorschrift

To a solution of 7-(2-chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one (0.18 g) and aminoguanidine hydrochloride (65 mg) in ethanol (10 ml) were added concentrated hydrochloric acid (0.12 ml) and water (0.12 ml), and the mixture was refluxed for 6 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution to make the solution alkaline. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate-methanol). The resulting crystals were dissolved in 1N hydrochloric acid (1 ml), and the solution was concentrated. The residue was recrystallized from ethanol-ethyl acetate to give 7-(2-chlorophenyl)-4-(4-chlorophenyl)-5-guanidinoimino-5,6,7,8-tetrahydrocinnoline hydrochloride (Compound 145) (0.13 g) as colorless crystals.

Quelle