Reaktion #1787797

Reaktionsgleichung

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

1-amino-3-hydroxyguanidine p-toluenesulfonate

hydrochloric acid

→

7-(2-furyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONto the residue were added ethyl acetate (30 ml), tetrahydrofuran (20 ml) and 0.2 N sodium hydroxide (20 ml)
3. 3
   workup.STIRRINGThe mixture was shaken
4. 4
   Waschenthe separated upper layer was washed with 0.2 N sodium hydroxide (10 ml) and water (10 ml, thrice)
5. 5
   workup.ADDITIONTo the upper layer was added 2 N hydrochloric acid (1 ml)
6. 6
   Einengenthe mixture was concentrated under reduced pressure
7. 7
   workup.STIRRINGThe residue in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 3 hours
8. 8
   Temperaturcooled
9. 9
   Sonstigecrystals precipitated
10. 10
    workup.STIRRINGwhile stirring
11. 11
    Filtrationwas filtered
12. 12
    Waschenwashed with ethanol
13. 13
    Sonstigedried

Vorschrift

A mixture of 7-(2-furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (227 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (314 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (30 ml), tetrahydrofuran (20 ml) and 0.2 N sodium hydroxide (20 ml). The mixture was shaken, and the separated upper layer was washed with 0.2 N sodium hydroxide (10 ml) and water (10 ml, thrice). To the upper layer was added 2 N hydrochloric acid (1 ml), and the mixture was concentrated under reduced pressure. The residue in ethanol (3 ml) was stirred at 90° C. (bath temperature) for 3 hours and cooled, and crystals precipitated while stirring was filtered, washed with ethanol and dried to give 7-(2-furyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 97) (154 mg) as pale yellow crystals.

Quelle