Aluminum(III) Chloride → 6-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 530335

反応式

HRID 530335 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH2:10][CH2:11]Cl)=[C:4]([Cl:14])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([Cl:14])[CH:3]=1)[NH:8][C:9](=[O:13])[CH2:10][CH2:11]2

参加物

3

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 43346898N-(4-bromo-2-chlorophenyl)-3-chloropropanamide

生成物 1

HCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one収率 27%

反応条件

温度
140 °C

実験手順

A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hr. After cooling to room temperature, the mixture was treated with ice-water slowly and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27% yield) as a white solid.

後処理

  1. customA flame-dried 500-mL flask equipped with a magnetic stirring bar
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-c48d1d1d9f234c3f86708cceda9c58a1
出典データセット
uspto-grants-2016_05
特許番号
US09353081B2

関連ノート

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