Nitric Acid → HCID 54573928, compound

Participants

Reaction Steps

6.16 g of adenosine-5'-carboxylic acid dimethylamide were dissolved at -40° C in 60 ml of fuming nitric acid (d = 1.50). A mixture, cooled to -20° C, of 30 ml of oleum and 30 ml of nitromethane was added dropwise to this solution within 30 minutes at such a rate that the temperature did not rise above -30° C. The mixture was stirred for 45 minutes at a temperature between -30° C and -25° C and then poured on to a solution of 325 g of potassium bicarbonate in 1 liter of water. By extraction with chloroform or with chloroform containing 5% n-propanol, there was obtained practically pure 2',3'-di-O-nitroadenosine-5'-carboxylic acid dimethylamide which melted at 156.5° C (decomposition) after recrystallisation from alcohol. The yield was 5.78 g (72.7% of theory).

Provenance & Evidence