N-(4-amino-3-methylphenyl)acetamide → 2-[(2-Methyl-4-acetamidophenyl)amino]-1-pyrroline

Participants

Reaction Steps

The product aniline of Example 32 was added to a solution of 2-chloro-1-pyrroline, prepared by the method of Example 1 using toluene, and the mixture was stirred for four hours at reflux. The solvent was removed by decanting and the residual solid was dissolved in water. The acidic solution (ca. pH 1.5) was washed with ethyl acetate and then made strongly basic (ca. pH 13) with aqueous sodium hydroxide. The crude product compound was immediately extracted into ethyl acetate. The extract was filtered and concentrated in vacuo to an oil, which solidified on standing. The solid was triturated with diethyl ether, collected, and dried under vacuum to give the title compound, the free base of the compound prepared by the methods of Example 16 and 17. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Provenance & Evidence