Reaction #3252

Reaction equation

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

hydrobromic acid

→

title compound

Yield 73.2%

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

Yield 73.2%

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed
2. 2
   Temperaturewith 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
   DryingThe chloroform layer was dried over magnesium sulfate
7. 7
   Otherevaporated
8. 8
   OtherThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and
9. 9
   Othercrystallized from cyclohexane

Procedure

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