Phosphorus oxychloride → 2-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

HRID 864639ノート

反応式

HRID 864639 の反応式
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[C:2]1=O.P(Cl)(Cl)([Cl:16])=O>[OH-].[NH4+]>[Cl:16][C:2]1[N:3]2[C:12]3[C:7]([CH2:6][CH2:5][CH2:4]2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:1]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 156467025,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

生成物 1

HCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline収率 65.8%

試薬・触媒・溶媒 1

HCID 14923Ammonium Hydroxide溶媒

実験手順

A slurry of 13.60 g of 5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one and phosphorus oxychloride (35 ml) was heated under reflux, with stirring, for 1.5 hrs and stirred at ambient temperature overnight. 10% Ammonium hydroxide (100 ml) and ice were added. The mixture was filtered, and the filtrate was extracted with dichloromethane. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated. The residue was purified by flash chromatography (silica; 10:1 dichloromethane-ethyl acetate). The appropriate fractions were collected and evaporated to give 9.90 g (65.8%) of product, mp 78° C.

後処理

  1. temperatureunder reflux
  2. stirringstirred at ambient temperature overnight
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with dichloromethane
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customThe residue was purified by flash chromatography (silica; 10:1 dichloromethane-ethyl acetate)
  10. customThe appropriate fractions were collected
  11. customevaporated

出典と根拠

ORDレコード
ord-9449b772754c43b3bcac2e407113962d
出典データセット
uspto-grants-1996_10
特許番号
US05563272

反応ノート

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