p-Aminoacetophenone → HCID 178467002, compound

Participants

Reaction Steps

A mixture of 14.5 gm. (0.107 moles) of p-aminoacetophenone and 19.0 gm. (0.097 moles) of ethyl (1-ethoxyformimidoyl)acetate hydrochloride (Chem. Ber., 100, 1428 (1967)) in 500 ml. of dry CH2Cl2 was stirred at 22° C. for 18 hours. The reaction, containing a precipitate of NH4Cl, was washed successively with ice cold aqueous solutions of 1 N HCl (2×100 ml), in Na2CO3 (2×100 ml) and saturated NaCl, and dried over Na.SO4. Filtration and evaporation yielded 20 gm. of crude ethyl [1-ethoxy(N-p-acetylphenyl)formimidoyl]acetate. This crude material was stirred and heated at 250° in 150 ml. of Dowtherm A for 30 minutes. Cooling dilution with 400 ml. of 1:1 ether-hexane and filtration of the precipitate yielded 12 gm. of the title compound. By base extraction of the filtrate and acidification, a further 2.5 gm. of product was obtained, mp. 210°-219° C. (65% yield).

Provenance & Evidence