Reaktion #3252

Reaktionsgleichung

6-(((dimethylamino)ethyl)amino)-3-methoxy-7H-indeno[2,1-c]quinoline-7-on

hydrobromic acid

→

title compound

Ausbeute 73.2%

6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on

Ausbeute 73.2%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed
2. 2
   Temperaturwith heat for 60 hours
3. 3
   workup.DISTILLATIONThe reaction mixture was distilled to dryness
4. 4
   workup.ADDITIONTo the residue was added water
5. 5
   Extraktionsubsequently extracted with chloroform
6. 6
   TrocknenThe chloroform layer was dried over magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and
9. 9
   Sonstigecrystallized from cyclohexane

Vorschrift

To a solution of 6-(((dimethylamino)ethyl)amino)-3-methoxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 1 (3 g, 8.6 mmol) in acetic acid (40 ml) was added 47% aqueous hydrobromic acid (40 ml), and the mixture was refluxed with heat for 60 hours. The reaction mixture was distilled to dryness. To the residue was added water and the solution was adjusted to a pH of about 8 with aqueous ammonia, and subsequently extracted with chloroform. The chloroform layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and crystallized from cyclohexane to give 2.1 g (yield: 73.0%) of title compound. The physicochemical properties thereof are shown in table 1.

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