N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide → 7-Chloro-3-methyl-1H-quinolin-2-one

HRID 1432847ノート

反応式

HRID 1432847 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:19])[C:10]([CH3:18])=[CH:11]C2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]=[C:10]([CH3:11])[C:9](=[O:19])[NH:8]2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 3497717N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 122780437-Chloro-3-methyl-1H-quinolin-2-one

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
120 °C

実験手順

To a solution of N-(3-chlorophenyl)-2-methyl-3-phenylacrylamide (2.5 g, 9.2 mmol) in chlorobenzene (50 mL) is added AlCl3 (6.2 g, 46 mmol). The solution is heated to 120° C. After 4 hours the solution is poured onto ice. The solution is filtered. The organic layer is washed with 1N HCl, H2O and saturated NaCl. The crude product is purified by column chromatography eluting with 2% MeOH/CH2Cl2. The title compound is obtained as a white solid (1.5 g, 7.74 mmol). 1H NMR (d6-DMSO, 300 MHz) δ11.82 (bs, 1H), 7.73 (s, 1H), 7.52 (m, 1H), 7.21 (m, 2H), 2.08 (s, 3H).

後処理

  1. additionAfter 4 hours the solution is poured onto ice
  2. filtrationThe solution is filtered
  3. washThe organic layer is washed with 1N HCl, H2O and saturated NaCl
  4. customThe crude product is purified by column chromatography
  5. washeluting with 2% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-644852ca47b5481583d39c05a0cc5fff
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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