Potassium Hydroxide → 5-Bromo-6-methoxy-7-methylquinoline

HRID 931743

Reaktionsgleichung

Reaktionsgleichung von HRID 931743
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]=[CH:8][CH:7]=[CH:6]2.C1C(=O)N([Br:21])C(=O)C1.[OH-].[K+]>OS(O)(=O)=O>[Br:21][C:4]1[C:3]([O:2][CH3:1])=[C:12]([CH3:13])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 155348986-Methoxy-7-methylquinoline

Produkt 1

HCID 666307145-Bromo-6-methoxy-7-methylquinolineAusbeute 171,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

To the solution of 6-methoxy-7-methylquinoline (4.28 g, 24.6 mmol) in 50 mL of concentrated H2SO4 was added NBS (4.41 g, 14.6 mmol) at 15° C., and the reaction was stirred at 15° C. for 3.5 hours. The reaction mixture was poured into ice-water (600 mL). The aqueous mixture was adjusted with a 50% KOH solution to pH ˜10, and then extracted with DCM (3×). The combined extract was dried with sodium sulfate. Concentration under reduced pressure gave 5-bromo-6-methoxy-7-methylquinoline (6.3 g). LCMS-ESI+ (m/z): 252.1, 254.1 (M+H)+.

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. extractionThe combined extract
  3. dry with materialwas dried with sodium sulfate
  4. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d86d0568b4504089a4e0b4b9adee75c9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296758B2

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