The reaction of β-N,N-Dialkylaminocrotonates with phosphorus oxychloride

Abstract

β-Dialkylaminocrotonates self-condense in excess phosphorus oxychloride at room temperature to give N,N-dialkylanthranilates in high yield. When stoichiometric amounts of phosphorus oxychloride are used and the reaction is carried out in benzene at 80°, significant amounts of phenolic by-products are also formed, which, in the case of β- morpholinocrotonates, become the major products. These compounds have been subjected to a number of transformations which establish their structure and at the same time provide methods of synthesis for N,N-dialkylaniline derivatives which are otherwise difficult to obtain.