2-Acetylpyrrole → HCID 18519882, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7.5 g (0.069 mole) of 2-acetylpyrrole, 17 g (0.089 mole) of 2-naphthalenoyl chloride and 18.3 (0.14 mole) of aluminum chloride in 200 mL of 1,2-dichloroethane was stirred for 4 h and then heated at 65° C. for 1.5 h. After cooling, the reaction mixture was poured into 2N HCl/ice. The organics were separated, washed with water, NaHCO3, water, brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized from EtOAc to give 9.25 g (51%) of 1-[4-(2-naphthalenoyl)-1H-pyrrol-2-yl]ethanone. mp 172-174° C. CIMS m/z 264 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.0-7.9 (Ar, 4H); 7.7-7.55 (Ar, 3H); 7.5 (Ar, 1H); 2.55 (s, 3H).

Provenance & Evidence