Nitroso derivs of N-methylaniline

Nitro Nitroso Derivatives of N- Methylaniline Nitro nitroso-N-methylanilines, C7H7N303, mw... 

Miller and Meyer, 1971). The gaseous products are the same as those derived from the reaction of nitrous acid with azide ion. The reaction is kinetically first order in each reactant, and it is likely that an intermediate complex is also formed in this case. Similarly a p-nitroso complex is formed from the same ruthenium nitrosyl and N-methylaniline, possibly by initial... 

Aliphatic and aromatic amines react with nitrous acid to form N-nitroso derivatives. For example, dimethylamine hydrochloride on treatment with sodium nitrite and hydrochloric acid is converted to nitrosodimethyl amine in 90% yield. In like manner, N-nitrosomethylaniline is synthesized from N-methylaniline in 93% yield. The ready formation of these derivatives and the easy reconversion to the amine by reduction affords an advantageous procedure for separating secondary amines from primary and tertiary amines, as shown in the synthesis of N-ethyl-m-toluidine and other N-alkyl derivatives by the alkylation of w-toluidine. ... 

When a solution of methylaniline in an acid is treated with nitrous acid, nitrosomethylanilinej C6H5.N(NO)CH3, is formed. The compound is a yellow oil of aromatic odor, which cannot be distilled without decomposition. It can be distilled with steam unchanged, however. On careful reduction it is converted into a derivative of hydrazine, C6H5N(CH3).NH2, and when treated with tin and hydrochloric acid, the nitroso group is eliminated and methylaniline is formed. 

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