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

HRID 530335

반응식

HRID 530335 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
140 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c48d1d1d9f234c3f86708cceda9c58a1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353081B2

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