3-chloro-N-(2-fluorophenyl)propanamide → 8-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

HRID 530331ノート

反応式

HRID 530331 の反応式
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>>[F:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

参加物

3

反応物 2

HCID 42560293-chloro-N-(2-fluorophenyl)propanamideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one収率 70.8%

反応条件

温度
160 °C

実験手順

A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with 3-chloro-N-(2-fluoro-phenyl)-propionamide (5.33 g, 26.5 mmol) and aluminium chloride (5.30 g, 39.7 mmol). In a pre-heated oil bath, the flask was heated at 160° C. for 1.5 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 title compound (3.1 g, 70% yield) as a solid. MS: 166.0 (M+H)+.

後処理

  1. customA flame-dried 50-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-e16845dd581e489eb0a4ee65399da6b9
出典データセット
uspto-grants-2016_05
特許番号
US09353081B2

反応ノート

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