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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.
Sodium amide is a handy reagent for the Chichibabin reaction but handling it can be dangerous and caution is advised. [4] σ-adduct (Meisenheimer adduct) formation; Evidence indicates that before addition of the amino group, the ring nitrogen atom is sorbed onto the surface of sodium amide and the sodium cation forms a coordination complex. [3]
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 ...
Amide reduction: Amines, aldehydes Reagent: lithium aluminium hydride followed by hydrolysis Vilsmeier–Haack reaction: Aldehyde (via imine) POCl 3, aromatic substrate, formamide Bischler–Napieralski reaction: Cyclic aryl imine: POCl 3, SOCl 2, etc. Tautomeric chlorination: Imidoyl chloride: Oxophilic halogenating agents, e.g. COCl 2 or SOCl 2
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the ...
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.