Potassium bis(trimethylsilyl)amide → 6-Bromo-4-hydroxy-1,5-naphthyridin-2(1H)-one

HRID 1478543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478543
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([NH:14][C:15]1[C:16]([C:22]([O:24]CC)=O)=[N:17][C:18]([Br:21])=[CH:19][CH:20]=1)(=[O:13])[CH3:12]>C1COCC1>[Br:21][C:18]1[N:17]=[C:16]2[C:15](=[CH:20][CH:19]=1)[NH:14][C:11](=[O:13])[CH:12]=[C:22]2[OH:24]

Komponenten

4

Edukt 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 90044467Ethyl 3-acetamido-6-bromopyridine-2-carboxylate

Produkt 1

HCID 900429756-Bromo-4-hydroxy-1,5-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of KHMDS (0.5 M in toluene, 27 ml, 14 mmol) at −78° C. was slowly added a solution of ethyl 3-acetamido-6-bromo-pyridine-2-carboxylate (1.3 g, 4.5 mmol) in THF (20 ml). Stirring was continued for 1 h at this temperature then the cooling bath was removed. Ethyl acetate followed by water was added at ambient temperature, then the phases were separated. The yellow aqueous phase was treated with HCl (1 M) until a colorless solid was formed. Filtration and washing of the solid with water followed by drying afforded 6-bromo-4-hydroxy-1H-1,5-naphthyridin-2-one as a colorless solid. The compound is exclusively present in the tautomer shown.

Aufarbeitung

  1. customthe cooling bath was removed
  2. additionwas added at ambient temperature
  3. customthe phases were separated
  4. additionThe yellow aqueous phase was treated with HCl (1 M) until a colorless solid
  5. customwas formed
  6. filtrationFiltration
  7. washwashing of the solid with water
  8. customby drying

Quellen und Nachweise

ORD-Eintrag
ord-d453ee0bbda44dab920dc6c73f81c1dc
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403845B2

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