Nitric acid Nitriles

Chlorosulfonic acid Saturated and unsaturated acids, acid anhydrides, nitriles, acrolein, alcohols, ammonia, esters, HCl, HF, ketones, hydrogen peroxide, metal powders, nitric acid, organic materials, water... 

As shown by the Italian school, the formation of isoxazole derivatives by the action of nitric acid or nitrogen oxides on acetylene derivatives and related reactions proceeds through intermediate nitrile oxides and must, therefore, be included with this type of synthesis. 

Very interesting transformations were reported in terminal alkynes RC=CH (R = alkyl, aryl, alkoxy, carboxylate, etc.). They react readily with nitric acid, in aqueous nitromethane (1 1) and in the presence of catalytic amounts of tetra-butylammonium tetrachloroaurate to give 3,5-disubstituted isoxazoles 15 in 35% to 50% isolable yield (92). The reaction might proceed via a nitrile oxide intermediate by attack of an electrophile (AuCh or H+) and of a nucleophile (N02 ) on the triple bond to form a vinyl nitrite, which is converted to a nitrile oxide by the action of gold(III) or of nitric acid (Scheme 1.8). 

Nitric acid, propyl ester, see Propyl nitrate Nitrile, see Acrylonitrile... 

Electrophilic nitrations of aliphatic nitriles, carboxylic acids,carboxylic esters, ° and /3-diketones have been reported. The nitration of 2-alkyl-substituted indane-l,3-diones with nitric acid, followed by alkaline hydrolysis, is a standard laboratory route to primary nitroalkanes. ... 

Hydrolysis of the diacetamides is effected by acids. Dilute hydrochloric, sulfuric and nitric acid have been used. An aldose with one carbon atom less than the original nitrile is then liberated from the combination. Only exceptionally can this aldose be isolated in pure condition without transforming it into an insoluble derivative in these instances, the method has been employed for preparative work. In most cases the sugar has been characterized as an osazone. The aldose, without great purification, has been employed successfully for reduction - or oxidation experiments. ... 

Iodobenzoic acid has been prepared by the oxidation of -iodotoluene with chromic acid mixture 1 and with nitric acid 2 from the nitrile obtained from -iodonitrobenzene and potassium cyanide 3 and from / -aminobenzoic acid by diazotization.4... 

Wear nitrile rubber gloves, laboratory coat, eye protection, and a face shield. A self-contained breathing apparatus may be necessary, depending on the size of the spill. Cover the spill with a 1 1 1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite), and sand. When the nitric acid has been absorbed, scoop the mixture into a plastic pail and, in the fume hood, very slowly add the mixture to a pail of cold water. Test the pH of the solution and neutralize if necessary with sodium carbonate. Decant the solution to the drain. Treat the solid residue as normal refuse.53... 

For production of niacinamide in the past, methylethylpyridine was oxidized with nitric acid to yield niacin, and P-picoline was treated with air and ammonia to produce the nitrile that was then hydrolyzed to niacinamide. A more modern process can produce both niacin and niacinamide from a single feedstock, either P-picoline or 2-methyl-5-ethylpyridine by oxidative ammonolysis, a combination of oxidation and animation. 

Dehydration of primary nitroalkanes with phenyl isocyanate or acetic anhydride in the presence of catalytic triethylamine affords nitrile oxides, which may be trapped as their 1,3-dipolar cycloadducts or allowed to dimerize to the corresponding furoxans. Other dehydrating agents that have been used include diketene, sulfuric acid and, when the a-methylene group is activated by electron-withdrawing groups, boron trifluoride in acetic anhydride, trifluoroacetic anhydride with triethylamine, and nitric acid in acetic acid. 

Acyl and perfluoroalkyl diazomethanes react with nitrogen oxides, and a-diazosulfones with nitrosyl chloride or dinitrogen trioxide, to give furoxans. The process is believed to involve nitrosation, followed by loss of nitrogen to form the nitrile oxide which subsequently dimerizes. Nitrosation of dimethylphenacylsulfonium bromide with nitric acid/sodium nitrite gives dibenzoylfuroxan. 

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