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

HRID 1082045ノート

反応式

HRID 1082045 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>>[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

3

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c241cc6340ae48d3b9ed93e5a06d7208
出典データセット
uspto-grants-1996_12
特許番号
US05589476

反応ノート

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