Réaction #3252

Équation de réaction

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

hydrobromic acid

→

title compound

Rendement 73.2%

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

Rendement 73.2%

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was refluxed
2. 2
   Températurewith 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
   Extractionsubsequently extracted with chloroform
6. 6
   SéchageThe chloroform layer was dried over magnesium sulfate
7. 7
   Autreevaporated
8. 8
   AutreThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and
9. 9
   Autrecrystallized from cyclohexane

Mode opératoire

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.

Source