Bromine → 5-Bromo-8-methoxy-2-methylquinoline

HRID 2393084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393084
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[CH:8]2.[Br:14]Br>CO>[Br:14][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11]2

Komponenten

4

Edukt 2

HCID 24408BromineHCID 3169868-Methoxy-2-Methylquinoline

Produkt 1

HCID 47150215-Bromo-8-methoxy-2-methylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 8-methoxy-2-methylquinoline (1.0 g) in methanol (30 ml) was treated at room temperature with bromine (0.31 ml). The mixture was heated at 45° C. for 2 hours and the reaction quenched with 5% aqueous sodium metabisulphite (50 ml). The solution was basified with 25% aqueous sodium hydroxide to pH13 and the product extracted with ethyl acetate (2×100 ml). The extracts were combined, dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was dissolved in ethyl acetate and passed through a silica pad. The solution was evaporated in vacuo to yield the desired product as an off-white solid (0.43 g).

Aufarbeitung

  1. customthe reaction quenched with 5% aqueous sodium metabisulphite (50 ml)
  2. extractionthe product extracted with ethyl acetate (2×100 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customThe solution was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7019cba75f449349a0c7c8c68bde685
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804588

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