Phosphorus oxychloride → 4-Chloro-3-nitro-1,5-naphthyridine

Participants

Reaction Steps

Phosphorus oxychloride (38 mL, 408 mmol) was added dropwise over a period of 70 minutes to a stirred suspension of 4-hydroxy-3-nitro[1,5]naphthyridine (60 g, 313.9 mmol). The orange suspension was stirred at ambient temperature for 5 hours and then poured into ice water (1.9 L) and stirred for 30 minutes. The solid was isolated by filtration, washed with water (3×200 mL), and then dissolved in dichloromethane (1.2 L). The solution was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 61.1 g of 4-chloro-3-nitro[1,5]naphthyridine as an orange solid.

Provenance & Evidence