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

HRID 726684

反応式

HRID 726684 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 193561156-(((dimethylamino)ethyl)amino)-3-fluoro-7H-indeno[2,1-c]quinoline-7-on dihydrochloride収率 68.6%

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2a4cc6d575b84c3a867f044cd90fdc78
出典データセット
uspto-grants-1998_01
特許番号
US05710162

関連ノート

読み込み中…