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Preparation of N-aryl-2-hydroxypropionamides from hydroxy aromatic compounds using a one-pot smiles rearrangement procedure

✍ Scribed by John J. Weidner; Philip M. Weintraub; Richard A. Schnettler; Norton P. Peet

Book ID: 104207772
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 554 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00314-1

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✦ Synopsis

Acylation of hydroxy aromatic compounds with 2-bromo-2-methylpropionamide followed by Smiles rearrangement of the resulting 2-aryloxypropionamide in a one-pot procedure produced the corresponding 2-hydroxy-2-methyI-N-arylpropionamides which can be converted to arylamines by hydrolysis. Particularly important applications of this new process were the conversions of estrone (6) and estradiol ( 14) to the corresponding 3-aminoestratriene derivatives 8 and 15, respectively. In addition, an improved Semmler-Wolff procedure is described for the conversion of 19-nortestosterone ( 22) to 3-aminoestra-l,3,5(10)-trien-17[~-ol hydrochloride (26).

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