An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P®)

Tetrahedron Letters

Volumn 52, Issue 10, 2011, Pages 1074-1077

  Augustine, John Kallikat ^a   Kumar, Rajesha ^a   Bombrun, Agnes ^b   Mandal, Ashis Baran ^a  

^a SYNGENE INTERNATIONAL LTD   (India)

^b MERCK SERONO S A   (Switzerland)

Author keywords

Acetanilides; Beckmann rearrangement; Ketoximes; Nitriles; Propylphosphonic anhydride

Indexed keywords

ACID ANHYDRIDE; ALDOXIME; AMIDE; NITRILE; PROPYLPHOSPHONIC ACID ANHYDRIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; ELECTROCHEMISTRY; GREEN CHEMISTRY; REACTION OPTIMIZATION; ROOM TEMPERATURE; SCREENING; SOLVENT EFFECT; SYNTHESIS;

EID: 79551681873     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.090     Document Type: Article

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40. All of the oxime substrates used in this investigation were synthesized in quantitative yields by refluxing a mixture of 1 equiv of the corresponding ketones or aldehydes, 1.6 equiv of hydroxylamine hydrochloride, and 2.0 equiv of sodium acetate in aqueous methanol.
41. 4. The solvent was removed under reduced pressure to afford the desired amides in good purity.
42. 4. The solvent was removed under reduced pressure to afford the desired nitriles in good purity.