Glycerol → 5-Bromo-8-methylquinoline

HRID 1027597

反応式

HRID 1027597 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].O[CH2:11][CH:12]([CH2:14]O)O.[N+](C1C=CC=CC=1)([O-])=O.[OH-].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]2[C:8]=1[CH:11]=[CH:12][CH:14]=[N:7]2

参加物

7

反応物 4

HCID 753GlycerolHCID 7416NitrobenzeneHCID 14798Sodium HydroxideHCID 27348055-Bromo-o-toluidine

生成物 1

HCID 47150225-Bromo-8-methylquinoline収率 67.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

A solution of 5-Bromo-2-methylaniline (7.44 g), glycerol (7.4 g), nitrobenzene (4.9 g) in 75% sulfuric acid (20 ml) was heated at 150° C. for 3 hrs. The solution was cooled to 0° C. then carefully neutralized with aqueous sodium hydroxide. The reaction mixture became a dark gum and was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with saturated brine, then dried with sodium sulphate and the solvent removed in vacuo. The crude product was purified by column chromatography (dichloromethane) to afford the title compound as a solid (6 g). 1H-NMR (CDCl3, 400 MHz) 8.91 (m, 1H), 8.51 (m, 1H), 7.7 (m, 1H), 7.50 (m, 1H), 7.4 (m, 1H), 2.72 (s, 3H).

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried with sodium sulphate
  4. customthe solvent removed in vacuo
  5. customThe crude product was purified by column chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-e8c82a859e60407184863d6af6fb5253
出典データセット
uspto-grants-2014_05
特許番号
US08735362B2

関連ノート

読み込み中…