P Nitrobenzenediazonium chloride

The concept and use of free radical attack on pyrimidines has been little developed. However, pyrimidine does react slowly with p-nitrobenzenediazonium chloride to yield some 2- and 4-p-nitrophenylpyrimidines (51JCS2323) in addition, 2,4-and 4,6-dimethyl-pyrimidine are converted by hydroxymethylene radicals (from ammonium peroxydisul-fate/methanol) into 6- and 2-hydroxymethyl derivatives, respectively (77H(6)525). Certain bipyrimidine photoproducts appear to be formed from two similar or dissimilar pyrimidinyl radicals (see Section 2.13.2.1.4). 

Nitrophenylarsonic acid has been prepared by heating p-nitrobenzenediazonium chloride with arsenious acid in hydrochloric acid, by the action of -nitrobenzenediazonium chloride on sodium arsenite, by the action of sodium arsenite on sodium -nitrobenzeneisodiazo oxide, by the diazotization of -nitro-aniline in acetic acid in the presence of arsenic chloride and cuprous chloride, and by the reaction of -nitrobenzenediazonium borofluoride with sodium arsenite in the presence of cuprous chloride. ... 

The product of the eoupling of (a) with p-nitrobenzenediazonium chloride is identieal with the p-nitrophenylhydrazone of [h). The oxidation of weostrychnidine to strychnidone by permanganate (1932) and of ncobrueidine to brucidone (1927) are probably analogous, and it is now found that by the aetion of p-nitrobenzenediazonium ehloride, neostrychnine is eonverted into stryehnone p-nitrophenylhydrazone. 

An a-demethylated product (116) is formed unexpectedly when the tetrasubstituted pyrrole (115) is reacted with p-nitrobenzenediazonium chloride <82JOC1750). M-f-Butylisoindole (117) couples with p-nitrobenzenediazonium fluoroborate to give the hydrazone (118) (80AG(E)320). 

Diphenylbenzodiazepine reacted with p-nitrobenzenediazonium chloride to give a yellow crystalline product that, from IR spectra, could be the p-nitrophenylhydrazone of 2,4-diphenylbenzodiazepin-3-one (59JCS... 

In some instances, diazo compounds and primary aromatic amines undergo an exchange reaction. Thus p-nitrobenzenediazonium chloride and aniline hydrochloride in a weakly acidic solution are converted to p-nitroaniline and benzenediazonium chloride... 

Eistert, B., Regitz, M. Japp-Klingemann cleavages. I. Cleavage of the coupling products of p-nitrobenzenediazonium chloride with carboxylic acid esters of tetrahydrothiopyran-3-one and thiophan-3-one. Ann. 1963, 666, 97-112. 

Bis-(p-nitrophenyl)antimony trichloride 526 Iron powder (2 g, 0.036 mole) is added at 0°, during 35-40 min, with vigorous stirring, to a solution of p-nitrobenzenediazonium chloride-1-antimony trichloride (15 g, 0.036 mole) in anhydrous acetone (45 ml), and the whole is then stirred for a further 40 min. The inorganic solid is removed and the filtrate is evaporated. The residual product is treated with 5N-hydrochloric acid (50 ml) and then with 96% ethanol (25-30 ml). The resulting mixture is poured into 5 % ammonia solution (excess) containing ice this precipitates bis-(p-nitrophenyl)stibinic acid (7 g, 97%), which is then converted into the trichloride by crystallization from 5N-hydrochloric acid. 

The substance contains an iV-methyl group, two active hydrogen atoms, and an aromatic methylenedioxj phenyl group. No methoxyl groups were found. Acetylation provided a neutral 0,iV -diacetate (A iax 1735 and 1650 cm i). Ismine condensed with p-nitrobenzenediazonium chloride to form a red dye, and it was suspected that the substance was represented by CCIII. Treatment of ismine (CCIII) first with acid and then... 

An ale. soln. of p-nitrobenzenediazonium chloride-stannic chloride and iodine in a quartz vessel stirred and irradiated under N2 through a Corning filter No. 9863 so that visible light, which halogens absorb, is eliminated p-nitro-phenyl iodide. Y 92.2% based on diazonium salt decomposed.—The yields are considerably higher than by other methods now available. F. e., also bromides, s. W. E. Lee, J. G. Calvert, and E. W. Malmberg, Am. Soc. 83, 1928 (1961). 

Methyl-3- (4 -nitrobenzyl) thiazolium bromide coupled with p-nitrobenzenediazonium chloride in phosphate buffer at pH 12.3 N-formyl-l-methyl-N-(4 -nitrobenzl) -2- (p-nitrophenylazothio)vinylamine. 

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