PREPARATION OF N-ARYL-2-HYDROXYPROPIONAMIDES FROM HYDROXY AROMATIC COMPOUNDS USING A ONE-POT SMILES REARRANGEMENT PROCEDURE

Abstract 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-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-1,3,5(10)-trien-17β-ol hydrochloride ( 26 ).