Methanol → Methyl 5-bromopyridine-3-carboxylate

HRID 52837

Reaktionsgleichung

Reaktionsgleichung von HRID 52837
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:11]O>Cl>[CH3:11][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 887075-Bromonicotinic acid

Produkt 1

HCID 699336Methyl 5-bromopyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

5-Bromo-nicotinic acid (5,00 g, 24.7 mmol) was dissolved in methanol (50 mL) and saturated with hydrochloric acid gas. The reaction mixture was allowed to stand for 2.5 days and then filtered. The filtrate was concentrated under reduced pressure and methylene chloride was added. The solution was washed with saturated sodium bicarbonate solution. The aqueous wash was back-extracted with methylene chloride (2x). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to afford 5-bromo-nicotinic acid methyl ester (4.72 g).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure and methylene chloride
  3. additionwas added
  4. washThe solution was washed with saturated sodium bicarbonate solution
  5. washThe aqueous wash
  6. extractionwas back-extracted with methylene chloride (2x)
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-482055b3c6d947c9bccd28c18aa9d287
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616714

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