6-bromo-N-methoxy-N-methylquinoline-2-carboxamide → 1-(6-Bromoquinolin-2-yl)ethanone

HRID 1693071노트

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HRID 1693071 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](N(OC)C)=[O:13])[CH:6]=[CH:5]2.[CH3:18][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](=[O:13])[CH3:18])[CH:6]=[CH:5]2

참가 물질

4

반응물 2

HCID 574581646-bromo-N-methoxy-N-methylquinoline-2-carboxamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 574581651-(6-Bromoquinolin-2-yl)ethanone수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 6-bromo-N-methoxy-N-methylquinoline-2-carboxamide (4.29 g, 14.5 mmol) in THF (100 ml) was added methyl magnesiumbromide (18.2 ml, 17.4 mmol, 0.96M in THF solution) at 0° C. dropwise and the mixture was stirred at 0° C. for 1 hour. Then, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml). After stirring for 30 min, the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (4:1), furnished the title compound (3.47 g, 96% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.66 (3H, s), 7.83-7.88 (1H, m), 8.02-8.20 (4H, m). MS (ESI): m/z 250, 252 (M+H)+.

후처리

  1. customThen, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml)
  2. stirringAfter stirring for 30 min
  3. extractionthe product was extracted with ethyl acetate which
  4. dry with materialwas dried over sodium sulfate
  5. filtrationThen, filtration, evaporation and purification through silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-5c2f439e379a49cfbcc06e98510a5a17
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158650B2

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