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Schmidt rearrangement

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The Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually a aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen

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Schmidt rearrangement

  1. 1. SCHMIDT REARRANGEMENT Touseef Haidar
  2. 2. Contoso S u i t e s Schmidt Reaction The Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually a aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen. 2
  3. 3. Contoso S u i t e s Schmidt Rearrangement The Schmidt reaction is an organic reaction in which and azide reacts with carbonyl derivative , usually a aldehyde, ketone, orcarboxylic acid, under acidic conditions to give an amine or amide with expulsion of nitrogen. The reaction is effective with carboxylic acids to give amines (above), and with ketones to give amides. 3
  4. 4. Contoso S u i t e s Inter & intra molecular rearrangement Carboxylic acids and hydrazoic acids react in presence of concentrated sulphuric acids to give amines. Schmidt reaction also occurs between ketones or aldehydes and hydrazoic acid. 4
  5. 5. Contoso S u i t e s Mechanism: 5
  6. 6. Contoso S u i t e s The reaction with acids i.e benzoic acid, which require heating for the removal of nitrogen from acid azide proceed. 6
  7. 7. Contoso S u i t e s 7
  8. 8. Contoso S u i t e s An alternative industrial synthesis method for paracetamol. It is involves direct acylation of phenol with acetic anhydride catalyzes by HF, conversion of the ketone to a ketoxime with hydroxylamine followed by the acid- catalyzed Beckmann rearrangement to give the amide. 8 Application in drug synthesis:
  9. 9. Contoso S u i t e s The backmamm rearrangement is also used in the synthesis of Nylon 6. 9 Applications in polymer synthesis:
  10. 10. Contoso S u i t e s • Methylation • Carboxylic acids • It is methylation agent for acidic compound such as carboxylic and mineral acid, carboxylic acids can be converted to esters. Reactivity of reagent increases with acidity. • Reaction is used where the acid is sensitive to higher temperature. 10 Application:
  11. 11. Contoso S u i t e s A synthetically useful example of this process is the conversion of 3.5 dinitrobenzoic acid (5) to 3,5- dinitroaniline (6) and cyclobutanecarboxylic acid (7) to cyclobutylamine (8). 11 Applications:
  12. 12. Contoso S u i t e s 1. Plagens, Andreas; Laue, Thomas M. (2005). Named organic reactions (2nd ed.). Chichester: John Wiley & Sons. 2. Wolff, Hans (2011). "The Schmidt Reaction". Organic Reactions 3. Nyfeler, Erich; Renaud, Philippe (24 May 2006). "Intramolecular Schmidt Reaction: Applications in Natural Product Synthesis". 4. J. H. Boyer & J. Hamer (1955). "The Acid-catalyzed Reaction of Alkyl Azides upon Carbonyl Compounds“ 5. Schmidt, K. F. (1924). "Über den Imin-Rest". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 12 Reference:
  13. 13. Contoso S u i t e s 13 Any Question?
  14. 14. Thank You April HanssonTOUSEEF HAIDAR +92 345 0134414 Syed.gerdezi@gmail.com

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