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

HRID 1082045Notes

Reaction equation

HRID 1082045 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>>[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

3

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]quinoline

Procedure

7.6 g (0.0436 mol) of 5,6-dihydro-4H-imidazo[4,5,1-ij]quino1-2(1H)-one are heated in the presence of 70 ml of phosphoryl chloride at the reflux 20 temperature for 3 hours. The solvent is evaporated to dryness and the residue is taken up in ice. The pH of the reaction mixture is adjusted to 8 with a concentrated sodium hydroxide solution and extraction is carried out with dichloromethane. The organic phase is dried over sodium sulphate and the solvent evaporated to dryness. The residue is purified by chromatography on a column of silica gel, the eluent being an ethyl acetate/hexane (30/70) mixture. There are obtained 5.8 g of product which is used as is in the following stage.

Workup

  1. temperaturereflux 20 temperature for 3 hours
  2. customThe solvent is evaporated to dryness
  3. extractionThe pH of the reaction mixture is adjusted to 8 with a concentrated sodium hydroxide solution and extraction
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. customthe solvent evaporated to dryness
  6. customThe residue is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-c241cc6340ae48d3b9ed93e5a06d7208
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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