Reaktion #2318391

Reaktionsgleichung

7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetic acid

phenylhydrazine

→

9-chloro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

Ausbeute 71.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed
2. 2
   Temperaturunder heating for 14 hours
3. 3
   workup.DISTILLATIONThen the ethanol is distilled off under reduced pressure, 100 ml of acetic acid
4. 4
   workup.ADDITIONis added to the residue
5. 5
   Temperaturthe mixture is refluxed
6. 6
   Temperaturunder heating for 7 hours
7. 7
   workup.DISTILLATIONAfter the acetic acid is distilled off
8. 8
   Extraktionthe residue is extracted with chloroform
9. 9
   WaschenThe extract is washed with water
10. 10
    Trocknendried over magnesium sulfate anhydride
11. 11
    workup.DISTILLATIONthe chloroform is distilled off
12. 12
    Sonstigeto give crystals
13. 13
    FiltrationThe precipitated crystals are collected by filtration
14. 14
    Sonstigerecrystallized from alcohol

Vorschrift

A mixture of 12 g of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetic acid and 8.1 g of phenylhydrazine in 150 ml of ethanol is refluxed under heating for 14 hours. Then the ethanol is distilled off under reduced pressure, 100 ml of acetic acid is added to the residue and the mixture is refluxed under heating for 7 hours. After the acetic acid is distilled off, the residue is extracted with chloroform. The extract is washed with water, dried over magnesium sulfate anhydride and then the chloroform is distilled off to give crystals. The precipitated crystals are collected by filtration and recrystallized from alcohol to give 11.1 g of 9-chloro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one as colorless prisms, melting at 120°-122° C.

Quelle