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

HRID 377597Notes

Reaction equation

HRID 377597 reaction equation
[Na].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][OH:6].Cl[C:9]1[C:18]2[C:19](=[O:29])[C:20]3[C:25]([C:17]=2[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)=[CH:24][C:23]1[O:26][CH2:27][O:28][C:22]=1[CH:21]=3>>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][O:6][C:9]1[C:18]2[C:19](=[O:29])[C:20]3[C:25]([C:17]=2[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)=[CH:24][C:23]1[O:26][CH2:27][O:28][C:22]=1[CH:21]=3

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 5360545SodiumHCID 193561276-chloro-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on

Product 1

HCID 193561446-(2-dimethylaminoethoxy)-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-onYield 68.1%

Conditions

Temperature
60 °C

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.

Workup

  1. customobtained in reference example 2
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=10:1(v/v)) and
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ad206548bf143b4b75981ad63487b2a
Source dataset
uspto-grants-2000_02
Patent number
US06028079

Reaction notes

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