Reaction #3255

Reaction equation

sodium

2-dimethylaminoethanol

6-chloro-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on

→

title compound

Yield 68.1%

6-(2-dimethylaminoethoxy)-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on

Yield 68.1%

Conditions

Workup

1. 1
   Otherobtained in reference example 2
2. 2
   Extractionextracted with chloroform
3. 3
   DryingThe chloroform layer was dried over magnesium sulfate
4. 4
   Otherevaporated
5. 5
   OtherThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=10:1(v/v)) and
6. 6
   Othercrystallized from ethyl acetate

Procedure

To a solution prepared with sodium (1.78 g, 77.4 mmol) and 2-dimethylaminoethanol (80 ml, 796 mmol) was added 6-chloro-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on (8 g, 25.8 mmol) obtained in reference example 2, and the mixture was stirred with heat at 60° C. for 24 hours. The reaction mixture was poured into ice water and 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=10:1(v/v)) and crystallized from ethyl acetate to give 6.37 g (yield: 68.1%) of title compound. The physicochemical properties thereof are shown in table 2.

Source