Reaction #3251

Reaction equation

6-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on

N,N-dimethylethylenediamine

→

title compound

Yield 68.6%

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

Yield 68.6%

Conditions

Workup

1. 1
   workup.DISTILLATIONThe reaction mixture was distilled to dryness
2. 2
   workup.ADDITIONTo the residue was added water and chloroform
3. 3
   Extractionfor extraction
4. 4
   DryingThe chloroform layer was dried over magnesium sulfate
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v))
7. 7
   workup.DISSOLUTIONThe purified material was dissolved in 20 ml of tetrahydrofuran
8. 8
   workup.ADDITIONTo the the solution was added 4N-hydrochloride/dioxane (2 ml)
9. 9
   Concentrationthe mixture was concentrated under reduced pressure
10. 10
    OtherThe residue obtained
11. 11
    Otherwas crystallized from diethylether

Procedure

To a suspension of 6-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on (860 mg, 3.0 mmol) in pyrydine (10 ml) was added N,N-dimethylethylenediamine (800 mg, 9.0 mmol), and the mixture was stirred with heat at 90° C. for 12 hours. The reaction mixture was distilled to dryness. To the residue was added water and chloroform for extraction. The chloroform layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)). The purified material was dissolved in 20 ml of tetrahydrofuran. To the the solution was added 4N-hydrochloride/dioxane (2 ml) and the mixture was concentrated under reduced pressure. The residue obtained was crystallized from diethylether to give 420 mg (yield 34.3%) of title compound. The physicochemical properties thereof are shown in table 1.

Source