Hydrochloric Acid → 1,6-Naphthyridin-5-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-azido-1,6-naphthyridine (3.4 g, 19.9 mmol) in methanol (40 mL) was added hydrochloric acid (30 mL). Stannous chloride dihydrate (22.5 g, 99.5 mmol) was added. The mixture was stirred at 75° C. for 3.5 h. A yellow precipitate formed. The mixture was filtered to give a yellow solid. The solid was suspended in EtOAc (200 mL). Sodium hydroxide (saturated aqueous solution) was added to adjust pH to 9. A white precipitate formed. The mixture was filtered and the filtrate was extracted with EtOAc (200 mL×6). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give 2.0 g of the crude product as a yellow solid. MS (ESI): m/z 146 [M+H]+.

Provenance & Evidence