Hydrochloric Acid → 2-(Azidocarbonyl)-5-(benzyloxy)-4-oxo-1,4-dihydropyridine

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Reaction Steps

A solution of concentrated hydrochloric acid (3 ml) in water (10 ml) was cooled to 0° C. and treated with 5-(benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridine (3 g, 11.58 mmole) to form a thick paste. A solution of sodium nitrite (1.68 g, 23.17 mmole) in water (30 ml) was added in 2 ml portions with mechanical swirling of the reaction vessel. The resulting mixture was stirred for 3.5 hours and filtered. The resulting pasty solid was washed with water, ice-cold ethanol, ether and hexane. After drying thoroughly under high vacuum, the yield of the title compound was 2.6 g.

Provenance & Evidence