Glycerol → 5-Bromo-8-methylquinoline

HRID 1027597

Reaktionsgleichung

Reaktionsgleichung von HRID 1027597
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 47150225-Bromo-8-methylquinolineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e8c82a859e60407184863d6af6fb5253
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735362B2

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