Reaktion #2145688

Reaktionsgleichung

9-chloro-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

piperazine

→

9-(1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride

Ausbeute 42.4%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated on an oil bath at 140° to 150° C. for 6 hours
2. 2
   SonstigeAfter completion of the reaction
3. 3
   Sonstigethe solvent was removed
4. 4
   workup.ADDITIONunder reduced pressure and 50 ml of water was added to the residue
5. 5
   workup.DISSOLUTIONto dissolve it
6. 6
   Sonstigethe water layer was separated
7. 7
   workup.ADDITIONtreated with activated carbon
8. 8
   Filtrationfiltered
9. 9
   workup.ADDITIONThe filtrate was again treated with activated carbon
10. 10
    Einengenfollowed by concentration
11. 11
    workup.ADDITIONThe addition of ethanol to the concentrate
12. 12
    Sonstigegave rise to crystals which
13. 13
    Sonstigewere recrystallized from ethanol-water

Vorschrift

20 ml of dimethyl sulfoxide was added to a mixture of 1.6 g of 9-chloro-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid and 3 g of anhydrous piperazine and the mixture was heated on an oil bath at 140° to 150° C. for 6 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure and 50 ml of water was added to the residue to dissolve it. The solution was shaken with 100 ml of chloroform and the water layer was separated and treated with activated carbon. The aqueous solution was rendered acidic with a 10% aqueous hydrochloric acid and filtered. The filtrate was again treated with activated carbon followed by concentration. The addition of ethanol to the concentrate gave rise to crystals which were recrystallized from ethanol-water to obtain 0.9 g of 9-(1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride as light yellow needles having a melting point of 269°-273° C. (decomposition).

Quelle