Cyanomethylnitrolic acid

Nitrosonitrocyanomethanides (NNtCM) can easily be synthesized in a two-step reaction (Scheme 18) (i) formation of the metastable cyanomethylnitrolic acid by nitrosation of nitroacetonitrile in water and extracting the cyanomethylnitrolic acid with ether, (ii) treating the dried ether solution of cyanomethylnitrolic acid with a solution of MOR (M = alkali metal, NR4 R = H, alkyl) in isopropanol results in a red precipitate of MNNtCM. The beautiful red alkali NNtCM salts can easily be purified by re-crystallization from methanol (yield 50-60%). 

Metastable cyanomethylnitrolic acid and its red color in basic water solution have already been observed by Steinkopf. Moreover, he postulated the existence of the silver salt AgNNtCM. The intermediate formation of the silver salt has also been postulated by Pillai and Boyer in the reaction of ICH2CN with AgN02 which finally gave NC—CH2—O—N=C(N02)CN, the only product which could be isolated . 

Cyanomethylnitrolic Acid (called Cyanmethyl-nitrolsaure orNitrooximinoessigsaurenitril in Ger) NC.C( NOH).NOz mw 115.05, N 36-53% hygr crysts, decomp on standing v sol in w, ale erh mod sol in benz si sol in chlf insol in petr eth was prepd from the Amm salt of nitro-acetonitrile in w by treatment with NaNO, Si H2S04. Its Silver salt, carmine-red microsc crysts explodes feebly when heated Refs l)Beil 2, 558 (242) 2)W.Steinkopf,... 

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