5- Nitro-2-halo-anilines

The reaction of anilines (R = H, m- and p-CHg, m- and p-halo-geno, W-NO2, P-OCH3, P-OC2H5) with 2-chloro-3-nitro-, 2-chloro-5-nitro-, 2-chloro-3-cyano-5-nitro-, 2-chloro-3-cyano-6-methyl-5-nitro-, and 2-chloro-3-cyano-4,6-dimethyl-5-nitro-pyridines. ... 

Electrochemically generated nickel is very selective for the reduction of ai compounds into anilines, in which alkenyl, alkyhyl, halo, cytino, formyl, ind benzyloxy groups are not affected. Sodium snlfide has been used for the selective reduction of at group in the presence of aliphatic nitro groups (Tq. 6.44. ... 

Schiff bases from substituted and unsubstituted benzaldehyde and aliphatic or aromatic amines are more stable [6-8]. Benzaldehyde substituents such as nitro, dialkylamino, hydroxyl, methoxyl, or halo have been used [7a-c]. Benzalaniline, m.p. 51°-52°C, is prepared in 87% yield by adding 1.0 mole of aniline to 1.0 mole of benzaldehyde at room temperature in the absence of a solvent. The crude product is added to alcohol [5] in order to induce crystallization [6]. 

Compounds which are vanishingly weakly basic in H20, such as nitro-anilines, nitro-aromatic or halo-nitro-aromatic compounds are protonated to a greater or less extent in superacids, allowing them to be used as indicators in Hammett Acidity Function measurements. Cl- which has essentially zero base strength in H20 is protonated by the superacids to HC1, which being monomolecular is expelled as a gas from the highly associated solvents. This provides a commonly-used important route to synthesis of anhydrous fluorides, fluorosulfates and triflates. 

Oxidations. Anilines substituted by halo, nitro, cyano, and alkylalkoxy groups arc oxidized by 1 in HO.Ac to the conesponding nitro compounds in 75-90% yield. Over-oxidation is usual when this oxidation is applied to anilines substituted by electron-donating groups. In successful reactions, yields are comparable to those obtained with CF,COjH (1, 821-822). 

Benzoic acids substituted with alkyl, halo, hydroxyl, alkoxyl, cyano, or nitro groups react to give the corresponding substituted anilines in 41-80% yields. The carboxyl group in an a-amino acid does not react with hydrazoic acid the reaction proceeds, however, if the amino group is further removed. This difference in reactivity is shown by the conversion of a-aminoadipic acid to i(-ornithlne (75%). ... 

Aniline, JV-alkyl-o-allyl-indole synthesis from, 4, 321 Aniline, N-allyl-indole synthesis from, 4, 326 Aniline, AT-allyl-o-bromo-indole synthesis from, 4, 327 Aniline, N-allyl-o-iodo-indole synthesis from, 4, 327 Aniline, o-bromo-in indole synthesis, 4, 340 Aniline, o-halo-cyclization, 4, 340 Aniline, m-nitro-in indole synthesis, 4, 338 Aniline black, 3, 197 Anilines... 

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