Chloroacetyl chloride → HCID 18519875, compound

Participants

Reaction Steps

A mixture of 12.82 g (0.058 mole) of 3-(2-naphthalenoyl)-1H-pyrrole, 7 mL (0.087 mole) of chloroacetyl chloride and 7.7 g (0.12 mole) of aluminum chloride in 500 mL of 1,2-dichloroethane was stirred at room temperature for 1 h. The reaction mixture was heated to reflux for 3 h. Another 7 g of aluminum chloride was added and refluxing continued for 1 h. After cooling, the reaction mixture was poured into 2 N HCl/ice, the organics were separated, washed with water, NaHCO3, water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and recrystallized from toluene to give 13.9 g (81%) of 2-chloro-1-[4-(2-naphthalenoyl)-1H-pyrrol-2-yl]ethanone. mp 175-177° C. CIMS m/z 299 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.0-7.85 (Ar, 4H); 7.7-7.5 (Ar, 4H); 4.6 (s, 2H).

Provenance & Evidence