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Schmidt reaction

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. It is named after Karl Friedrich Schmidt (1887–1971), who first reported it in 1924 by successfully…

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Reaction mechanism

Curtius rearrangementFischer esterificationSulfuric acidAcyliumProtonation
15 related topics

Overview

Organic chemistryOrganic reactionAzideCarbonylAldehyde
15 related topics

Reactions involving alkyl azides

Azides3-nitrobenzaldehydeAnnulationLactamsAlkaloids
5 related topics

Reactions involving nitromethane (CH3NO2)

Nef reactionLewis acidBrønsted acid
3 related topics

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Overview

Reaction mechanism

Reactions involving alkyl azides

Reactions involving nitromethane (CH3NO2)

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Schmidt reaction

Nodes43
Edges42
Triples48
Avg. degree1.95
Density0.046512
Components1

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Schmidt reaction

Top relations

related to Reactions involving nitromethane (CH3NO2) · 19
Schmidt reaction → AcOH, Beckmann-type, Brønsted, Finally, H2O, HCO2H, HNO, HOTf, In, Jiao, Lewis, N-donor, Nef, O-acetyl, Schmidt, Schmidt-Jiao, Subsequently, The, With Tf2O
related to Reaction with ketones · 13
Schmidt reaction → Attack, Baeyer, Baeyer-Villiger, Beckmann, H2SO4, HCl, In, It, Loss, One, Schmidt, These, Villiger
related to Reaction with acids · 8
Schmidt reaction → An, C-N, Curtius, Fischer, In, Reaction, Schmidt, The
related to Reactions involving alkyl azides · 7
Schmidt reaction → Boyer, R-N3, Schmidt, The, These, This, Variations
is a · 1
Schmidt reaction → organic reaction in which an azide reacts with a carbonyl derivative

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Important terminology

reaction acid schmidt give amide rearrangement carboxylic acids azide ketones protonated intermediate conditions reported reactions alkyl nitromethane nitrogen loss water

Entity relationships Subject–Predicate–Object triples

SubjectPredicateObjectConfidenceSrc
Schmidt reactionis aorganic reaction in which an azide reacts with a carbonyl derivative0.90text
Schmidt reactionrelated to Reaction with acidsThe0.60section
Schmidt reactionrelated to Reaction with acidsCurtius0.60section
Schmidt reactionrelated to Reaction with acidsFischer0.60section
Schmidt reactionrelated to Reaction with acidsAn0.60section
Schmidt reactionrelated to Reaction with acidsIn0.60section
Schmidt reactionrelated to Reaction with acidsSchmidt0.60section
Schmidt reactionrelated to Reaction with acidsReaction0.60section
Schmidt reactionrelated to Reaction with acidsC-N0.60section
Schmidt reactionrelated to Reaction with ketonesIn0.60section
Schmidt reactionrelated to Reaction with ketonesSchmidt0.60section
Schmidt reactionrelated to Reaction with ketonesOne0.60section

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