1,1-Dichloroethane → 8-Chloro-1,5-naphthyridin-3-ol

HRID 40365

Reaktionsgleichung

Reaktionsgleichung von HRID 40365
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12]C)=[CH:7]2.B(Br)(Br)Br.ClC(Cl)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2

Komponenten

5

Edukt 3

HCID 63651,1-DichloroethaneHCID 25134Boron tribromideHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Produkt 1

HCID 1357435768-Chloro-1,5-naphthyridin-3-olAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (2.5 g, 12.8 mmol), boron tribromide (13.4 mL, 141.3 mmol) and dichloroethane (0.6M, 21.4 mL). Vessel sealed and mixture stirred at 60° C. for 16 hrs. Next day the reaction mixture was chilled in ice bath and diluted with dichloromethane (200 mL). This was allowed to sit under nitrogen system until all fuming ceased. The resulting yellow solid material was then filtered and dried under high vacuum. This was suspended in 40% (90:10:1 DCM/MeOH/NH4OH)/DCM and purified in this system by ISCO silica gel chromatography (80 g) afford 8-chloro-1,5-naphthyridin-3-ol (1.3 g, 56% yield). MS [M+H]=181.2. Calc'd for C8H5ClN2O=180.59.

Aufarbeitung

  1. customVessel sealed
  2. temperatureNext day the reaction mixture was chilled in ice bath
  3. filtrationThe resulting yellow solid material was then filtered
  4. customdried under high vacuum
  5. custompurified in this system by ISCO silica gel chromatography (80 g)

Quellen und Nachweise

ORD-Eintrag
ord-6f4a85c5f5fa432aa161793f77ea5d01
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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