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

HRID 864639노트

반응식

HRID 864639 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 14923Ammonium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9449b772754c43b3bcac2e407113962d
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563272

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