Ammonia → 4-(4,5-dihydro-1,3-oxazol-2-yl)aniline

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Reaction Steps

Using known procedures for the synthesis of cyclic imino ethers from nitriles (18,26), 4-aminobenzonitrile was treated with an excess of 2-aminoethanol (1 part nitrile/2 parts aminoalcohol) in refluxing xylene, with 3.5 wt. % zinc acetate catalyst, with all under a slow nitrogen stream. The solution was heated until no NH3 was detected in the off gas. After removal of the xylene, the crude solid product was obtained in high yield. The crude product was recrystallized from acetonitrile to obtain an 82% yield of white, crystalline 4-APOXO having mp 163-165° C., reported 158-160° C. The structure of the monomer was confirmed by FT-IR and 1H NMR. Structure of 4-APOXO is as follows:

Provenance & Evidence