Pyridine, hydrofluoride (1:1) → HCID 178517850, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL round bottom flask was added 5-chloro-6-ethoxy-1,7-naphthyridin-8-amine (1.03 mmol), followed by hydrogen fluoride pyridine (5 mL). The solution was cooled to 0° C., then sodium nitrite (1.23 mmol) was added in portions. The mixture was warmed to room temperature over a period of 1 h. The reaction was then neutralized with saturated NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The resultant crude residue was dissolved in dichloroethane (50 mL), then AlCl3 (820 mg, 6.18 mmol) was added in one portion. The mixture was refluxed for 2 h under Ar. The solution was allowed to cool to room temperature, then diluted with water. The aqueous phase was extracted with ethyl acetate, the organic layer was washed with brine then dried over Na2SO4. The solvent was concentrated to yield 5-chloro-8-fluoro-1,7-naphthyridin-6-ol (180 mg, 88%) as a pale yellow solid. LC/MS m/z 199 [M+H].

Provenance & Evidence