Glycerol → 5-Bromo-8-methylquinoline

HRID 1027597

반응식

HRID 1027597 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 47150225-Bromo-8-methylquinoline수율 67.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e8c82a859e60407184863d6af6fb5253
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735362B2

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