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

HRID 1432847노트

반응식

HRID 1432847 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-644852ca47b5481583d39c05a0cc5fff
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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