2-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone → 2-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone

Participants

Reaction Steps

A solution of 10 g (0.034 mole) of 2-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone and 3.8 g (0.041 mole) sodium diformylamide in 80 mL acetonitrile was heated under reflux overnight under argon. An additional 2.0 g portion of sodium diformylamide was added and reflux was continued for 1.5 hrs. After evaporation of the solvent in vacuo the residue was passed through a flash column (silica gel, 3:1 hexane:acetone the 2:1 hexane:acetone) to give 6.18 g of a solid. mp 279-282° C. 260° C. decomp. mass spectrum (Cl—CH4) m/z=333 (M+1). NMR 300 MHz (CDCl3) d 9.0 (s, 2 H); 7.8 (d, 2 H); 7.55 (s, 1 H); 7.45 (d, 2 H); 7.1 (s, 1H); 4.85 (s, 2 H); 4.1 (s, 3 H).

Provenance & Evidence