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

HRID 1095667

反応式

HRID 1095667 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 109330948-Bromo-1,2-dihydroquinolin-2-one収率 65%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b6c5860b1e9b4a00b921c599e6b0883c
出典データセット
uspto-grants-2012_03
特許番号
US08138181B2

関連ノート

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