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

Article abstract of DOI:10.1016/S0040-4020(97)00314-1

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).