M-Nitraniline

The yield of m-nitraniline when prepared as described above is only about four-fifths of the theoretically possible amount. This indicates, quite clearly, that the intermediate reduction products are reduced further much more rapidly than is an intact nitro-group. 

A mixture of equimolecular amounts of m-nitraniline (69.0 g), methacrylic acid (43.0 g), and pyridine (39.5 g) was heated to 125°C for 20 h, and was then poured into 500 ml water. A semi-crystalline product separated from the liquid. The supernatant liquid was decanted and 500 ml fresh water was added. The pH was adjusted to 7-7.5 by means of sodium hydroxide. The precipitate was filtered with suction and washed with water. When the filtrate was acidified with acetic acid, a precipitate of N-(3-nitrophenyl)-p-amino-isobutyric acid was formed. When filtered, washed with water and dried, it weighed 56.0 g and had a melting point of 130°-131°C (recryst. from alcohol). The yield was 50% based on nitraniline. 

Since the tendency to form quinone derivatives is lacking in m-nitraniline, the nitroso- and hydroxylamine phase can unite normally to the, azo-body. 

This, however, is not the case, as the former has a moment of6 67,D and the latter one of 5.22, D, which is close to the vectorial sum of the moments in m-nitraniline. It will be evident from the above examples, that the conditions of resonance in the various positions of the rings are not the same. In monosubstituted naphthalenes there are seven possible valence bond structures with a separation of charge in the case of the a derivatives and only six for the p derivatives, viz... 

A soln. of m-nitraniline in glacial acetic acid stirred into a soln. 

Niter. See Potassium nitrate Nitramin. See 2-Amino-5-nitrothiazole Nitramyl. See Isoamyl nitrite 4-Nitraniline. See p-Nitroaniline m-Nitraniline. See m-Nitroaniline o-Nitraniline. See o-Nitroaniline p-Nitraniline. See p-Nitroaniline Nitrapyrin. See 2-Chloro-6-(trichloromethyl) pyridine... 

Synonyms 1-Amino-3-nitrobenzene m-Aminonitrobenzene Cl 37030 Diazo Fast Orange R Fast Orange m-Nitraniline m-Nitroaminobenzene 3-Nitroaniline 3-Nitrobenzeneamine m-Nitrophenylamine... 

Protection of carboxyl groups with m-nitraniline—Inverse addition s. 11, 481... 

A soln. of m-(hydroxymethyl) phenoxyacetic acid in thionyl chloride refluxed 3 hrs., evaporated in vacuo, the residue dissolved in ethylene dichloride, and again evaporated in vacuo —crude m-(chloromethyl) phenoxyacetyl chloride (Y 96%) dissolved in methylene chloride, a soln. of 2 moles of m-nitraniline in the same solvent added with stirring during ca. 15 min., stirring continued for 10 min., treated with anhydrous HCl until the yellow color of free m-nitraniline has disappeared, filtered, crude 2-[(m-chloromethyl)phenoxy]-3 -nitro-acetanilide isolated from the filtrate, dissolved in chloroform containing diethanolamine, and refluxed 6 hrs. 2-(m-[bis-(2-hydroxyethyl) aminomethyl]-... 

Benzoylbenzylideneanilines. A soln. of 4-benzoylbenzaldehyde and m-nitraniline in benzene containing a little p-toluenesulfonic acid refluxed with azeotropic water entrainment until water separation is complete product. Y 70%. F. e., also without p-toluenesulfonic acid, s, H. Dehne and H.-H. Ruttinger, Z. Chem. 11, 462 (1971). 

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