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

HRID 377593

Reaktionsgleichung

Reaktionsgleichung von HRID 377593
[Cl:1][C:2]1[C:11]2[C:12](=[O:19])[C:13]3[C:18]([C:10]=2[C:9]2[C:4](=[CH:5][C:6]([F:20])=[CH:7][CH:8]=2)[N:3]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>>[ClH:1].[ClH:1].[CH3:21][N:22]([CH2:23][CH2:24][NH:25][C:2]1[C:11]2[C:12](=[O:19])[C:13]3[C:18]([C:10]=2[C:9]2[C:4](=[CH:5][C:6]([F:20])=[CH:7][CH:8]=2)[N:3]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:26]

Komponenten

3

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 193561006-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on

Produkt 1

HCID 193561156-(((dimethylamino)ethyl)amino)-3-fluoro-7H-indeno[2,1-c]quinoline-7-on dihydrochlorideAusbeute 68,6 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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 solotion 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.

Aufarbeitung

  1. distillationThe reaction mixture was distilled to dryness
  2. additionTo the residue was added water and chloroform
  3. extractionfor extraction
  4. dry with materialThe chloroform layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v))
  7. dissolutionThe purified material was dissolved in 20 ml of tetrahydrofuran
  8. additionTo the the solotion was added 4N-hydrochloride/dioxane (2 ml)
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue obtained
  11. customwas crystallized from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-c9069b0fa39b4b12be2978b17542c13b
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028079

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