تفاعل #3252

معادلة التفاعل

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

hydrobromic acid

→

title compound

المردود 73.2%

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

المردود 73.2%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed
2. 2
   درجة الحرارةwith 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
   استخلاصsubsequently extracted with chloroform
6. 6
   تجفيفThe chloroform layer was dried over magnesium sulfate
7. 7
   أخرىevaporated
8. 8
   أخرىThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:water=8:3:1(v/v/v)) and
9. 9
   أخرىcrystallized from cyclohexane

الإجراء التجريبي

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.

المصدر