Acetonitrile → HCID 57447078, compound

Participants

Reaction Steps

Ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butyrate (86.2 g, 0.276 mol), sodium azide (35.49 g, 0.552 mol), and cerium chloride heptahydrate (50.86 g, 0.138 mol) were triturated in a 9:1 mixture of acetonitrile:water (1012 mL). The reaction mixture was stirred and heated to reflux for 18 hours. The reaction was filtered while still hot and the yellow filtrate was concentrated under reduced pressure to yield 90.94 g of crude product. The material was triturated at 95° C. with 360 mL ethyl acetate and filtered. The filtrate produced pale yellow crystals at ambient temperature to afford 64.3 g of ethyl 4-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]butyrate as a yellow solid.

Provenance & Evidence