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

HRID 1693071ノート

反応式

HRID 1693071 の反応式
[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

参加物

4

反応物 2

HCID 574581646-bromo-N-methoxy-N-methylquinoline-2-carboxamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 574581651-(6-Bromoquinolin-2-yl)ethanone収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5c2f439e379a49cfbcc06e98510a5a17
出典データセット
uspto-grants-2012_04
特許番号
US08158650B2

反応ノート

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