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

Participants

Reaction Conditions

Reaction Steps

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (1200 mg, 6166 μmol), boron tribromide (6412 μl, 67825 μmol) and dichloroethane (10277 μl, 6166 μmol). The vessel was sealed and the mixture was stirred at 60° C. for 16 h. The reaction mixture was carefully diluted with DCM, and the solids were filtered. The crude material was purified by silica gel chromatography with 40-70% (90:10:1 DCM/MeOH/NH4OH)/DCM to afford 8-chloro-1,5-naphthyridin-3-ol. MS: [M+H]=181.

Provenance & Evidence