N-(2-Bromophenyl)cinnamamide → 8-Bromo-1,2-dihydroquinolin-2-one

HRID 1095667

반응식

HRID 1095667 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]2

참가 물질

4

반응물 2

HCID 764332N-(2-Bromophenyl)cinnamamideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 109330948-Bromo-1,2-dihydroquinolin-2-one수율 65%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

반응 조건

온도
100 °C

실험 절차

A mixture of N-(2-bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 100° C. for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65% yield) MS ESI (+) m/z 224 and 226 (M+1 of each isotope) detected.

후처리

  1. temperatureby cooling to ambient temperature overnight
  2. temperatureto warm to ambient temperature over 1 hour
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solids were triturated with 1000 ml hexanes
  7. customdried

출처 및 근거

ORD 기록
ord-b6c5860b1e9b4a00b921c599e6b0883c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138181B2

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