Phosphorus oxychloride → 5-Chloro-4-nitrotetrazolo[1,5-a]quinoline

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, POCl3 (16.42 ml, 0.17 mol) was slowly added to a chilled (0° C.) flask containing N,N-dimethylformamide (100 ml). The resulting solution was slowly warmed to room temperature and then added dropwise to a suspension of 4-nitro-tetrazolo[1,5-a]quinolin-5-ol in N,N-dimethylformamide (300 ml). The reaction was heated to 100° C. for 30 minutes. The orange/red solution was quenched by pouring over 1 liter of ice water. A yellow precipitate formed and was collected by filtration, redissolved in chloroform (approx. 750 ml), dried (Na2SO4), filtered, and concentrated in vacuo to yield 33.74 g of 5-chloro-4-nitrotetrazolo[1,5-a]quinoline as a yellow solid.

Provenance & Evidence