109185-21-9Relevant articles and documents
PROCESS FOR ALKYLATING AND SMILES REARRANGEMENT OF HYDROXY AROMATICS
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, (2008/06/13)
The present invention is a process of converting a hydroxy aromatic into a 2-hydroxy-N-arylacetamide, comprising: (1) treating a reaction mixture comprising a salt of a hydroxy aromatic with an alkylating agent; and (2) treating the reaction mixture with
Preparation of N-Aryl-2-hydroxypropionamides from hydroxy aromatic compounds using a one-pot smiles rearrangement procedure
Weidner, John J.,Weintraub, Philip M.,Schnettler, Richard A.,Peet, Norton P.
, p. 6303 - 6312 (2007/10/03)
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-methyl-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-aminoestrahriene derivatives 8 and 15, respectively. In addition, an improved Semmler-Wolff procedure is described for the conversion of 19-nortestosterone (22) to 3-aminoestra-1,3,5(10)-uien-17β-ol hydrochloride (26).