Aluminum(III) Chloride → 6-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 530340노트

반응식

HRID 530340 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH2:10][CH2:11]Cl)=[CH:4][C:3]=1[Cl:14].[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[Cl:14])[NH:8][C:9](=[O:13])[CH2:10][CH2:11]2

참가 물질

3

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 86679184N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide

생성물 1

HCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one수율 50.3%

실험 절차

A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (1.0 g, 3.36 mmol) and aluminium chloride (0.67 g, 5.04 mmol). In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr. After cooling to room temperature, the reaction 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. After evaporation of the solvent, the residue was purified by recrystallization in EtOAc (2 mL) and gave title compound (0.44 g, 50% yield) as a solid. MS: 260.0 (M+H)+.

후처리

  1. customA flame-dried 50-mL flask equipped with a magnetic stirring bar
  2. temperatureIn a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. customdried over anhy
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by recrystallization in EtOAc (2 mL)

출처 및 근거

ORD 기록
ord-1991a92e488540498ca369e2a41e59f7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353081B2

반응 노트

불러오는 중…