Water → 5-Azido-1,6-naphthyridine

HRID 1615694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615694
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C=O)C>[N:12]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)=[N+:13]=[N-:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 122042345-Chloro-1,6-naphthyridine

Produkt 1

HCID 866678085-Azido-1,6-naphthyridineAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-chloro-1,6-naphthyridine (3.3 g, 20.1 mmol) in DMF (40 mL) was added sodium azide (6.0 g, 88.5 mmol). The mixture was stirred at 80° C. for 4 h. The mixture was then poured into water (120 mL). The aqueous phase was extracted with EtOAc (150 mL×4). The combined organic layers were washed with brine (100 mL×3), dried over sodium sulfate, and concentrated under reduced pressure to give 3.4 g of the crude product as a brown solid. ESI MS: m/z 172 [M+H]+.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc (150 mL×4)
  2. washThe combined organic layers were washed with brine (100 mL×3)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7f14999d961148c284caa2df2539048a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765760B2

Notizen zur Reaktion

Wird geladen…