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Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group. [ 1 ] [ 2 ] Catalytic hydrogenation
The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
This process was originally described by Ritter in 1948, [11] and an estimated 10,000 tons/y (year: 2000) of this and related lipophilic amines are prepared in this way. [12] Otherwise, the Ritter reaction is most useful in the formation of amines and amides of pharmaceutical interest.
In their synthesis of the antiviral drug oseltamivir, also known as Tamiflu, Ishikawa et al. used the Curtius rearrangement in one of the key steps in converting the acyl azide to the amide group in the target molecule. In this case, the isocyanate formed by the rearrangement is attacked by a carboxylic acid to form the amide.
Weerman degradation, also named Weerman reaction, is a name reaction in organic chemistry.It is named after Rudolf Adrian Weerman, who discovered it in 1910. [1] In general, it is an organic reaction in carbohydrate chemistry in which amides are degraded by sodium hypochlorite, forming an aldehyde with one less carbon. [2]
The secondary amide 1 reacts via its enolized form with phosphorus pentachloride to form the oxonium ion 2. This produces a chloride ion which deprotonates the oxonium ion to form and imine 3 and hydrogen chloride. These then react with one another to form an amine, with loss of the phosphorus chloride residue.
The vast majority of these procedures utilize the commercially available salt N,O-dimethylhydroxylamine hydrochloride [MeO(Me)NH•HCl], which is typically easier to handle than the free amine. [6] Treatment of an ester or lactone with AlMe 3 or AlMe 2 Cl affords the corresponding Weinreb amide in good yields. Alternatively, non-nucleophilic ...
In the third step, an isomerization step protonates the nitrogen atom leading to the amide. The Beckmann rearrangement mechanism The same computation with a hydroxonium ion and 6 molecules of water has the same result, but when the migrating substituent is a phenyl group, the mechanism favors the formation of an intermediate three-membered π ...