Nitrous acid, reaction with amides primary amines

If primary or secondary amines are used, A/-substituted amides are formed. This reaction is called aminolysis. Hydra2ines yield the corresponding hydra2ides, which can then be treated with nitrous acid to form the a2ides used in the Curtius rearrangement. Hydroxylamines give hydroxamic acids. 

An indirect method of hydrolyzing some amides utilizes nitrous acid. Primary amides are converted easily to carboxylic acids by treatment with nitrous acid. These reactions are very similar to that which occurs between a primary amine and nitrous acid (Section 23-10) ... 

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