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

HRID 864639Notes

Reaction equation

HRID 864639 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9449b772754c43b3bcac2e407113962d
Source dataset
uspto-grants-1996_10
Patent number
US05563272

Reaction notes

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