Nitrous acid (HNO 2 or HONO) reacts with aliphatic amines in a fashion that provides a useful test for distinguishing primary, secondary and tertiary amines. Amine - Amine - Reactions of amines: Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. I am looking forward for the most plausible mechanism of the reaction between acid amide (derivative of carboxylic acid) and HNO2. I am only a second semester o-chem undergrad so don't take my word as fact, however the reaction with ethanamide and nitrous acid sounds like a diazotization which results from the reaction of the primary amine, sodium nitrate, and 2 moles of HCl. although i know the general reaction ar written in my book ie. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. ChemInform Abstract: REACTION OF AMINOQUINONES AND RELATED VINYLOGOUS AMIDES WITH NITROUS ACID. The nitrous acid usually arises from protonation of nitrite. When a primary amine reacts with nitrous acid, the product is either an alcohol or an alkene, but the more interesting part about the reaction is that nitrogen gas is liberated as well.

That is exactly what happens when amides are hydrolysed in the presence of dilute acids such as dilute hydrochloric acid. They are usually produced by the reaction of nitrous acid (HNO 2) and secondary amines.. HONO + R 2 NH → R 2 N-NO + H 2 O. The initial reaction is followed by treatment with dilute acid, such as dilute sulphuric or hydrochloric acid. There is no reaction I can think of that involves amides and nitrous acid. ... however the reaction with ethanamide and nitrous acid sounds like a diazotization which results from the reaction of the primary amine, sodium nitrate, and 2 moles of HCl. Reaction of Amines with Nitrous Acid. As NH2 is a poor leaving group and the amides RCONH2 are stabilized through a resonance, they generally are not reactive in a sense of hydrolysis, hence necessitating harsh conditions and strong acids.
Its nitrogen has only three pairs of electrons in the valence shell, so it is a very good electrophile, very susceptible to attack by a nucleophile. Reaction of Secondary Amines with Nitrous Acid. The closest thing I can come up with from introductory organic chemistry is the synthesis of carbolic acid (phenol) from aniline, which is an amine not an amide. The alkaline hydrolysis of amides actually involves reaction with hydroxide ions, but the result is similar enough that it is still classed as hydrolysis. One of the most common methods to make an amide is to take a carboxylic acid and convert it to an acid chloride by using thionyl chloride (SOCl 2). For example, if you reduce ethanamide, you will get ethylamine. Chemischer Informationsdienst 1976, 7 (13) , no-no. The reaction of secondary amines with nitrous acid can be summarized in the first part of the arene diazonium, salt formation. Amides can be reduced to primary amines by reaction with lithium tetrahydridoaluminate, LiAlH 4, in dry ether (ethoxyethane) at room temperature. Salt formation is instantly reversed by strong bases such as NaOH. Nitrous acid is formed, but it reacts further with acid to make water and the nitrosyl cation.
Reactions of Amides How to Make an Amide.

SYNTHESIS AND CHEMISTRY OF CYCLIC DIAZO KETONES. The organic chemistry of nitrosamines is well developed both with regard to their syntheses, their structures, and their reactions. The acid acts as a catalyst for the reaction between the amide and water.

The reduction of amides. The nitrosyl cation is electron deficient. Reactions of Amines (continued) 4.

Reaction of amide with nitrous acid? DOI: 10.1002/chin.197613251.

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