Reacción #3252

Ecuación de reacción

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

hydrobromic acid

→

title compound

Rendimiento 73.2%

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

Rendimiento 73.2%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed
2. 2
   Temperaturawith 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
   Extracciónsubsequently extracted with chloroform
6. 6
   SecadoThe chloroform layer was dried over magnesium sulfate
7. 7
   Otroevaporated
8. 8
   OtroThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and
9. 9
   Otrocrystallized from cyclohexane

Procedimiento

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.

Fuente