Hydrochloric Acid → 2-Chloro-1-[5-(4-nitrobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone

Participants

Reaction Steps

A 210 g (1.57 mole) sample of AlCl3 was added in portions to a solution of 145.4 g (0.63 mole) of (1 -methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-methanone (1) in 450 mL of 1,2-dichloroethane (DCE). A solution of 125 mL (1.57 mole) of chloroacetyl chloride in 200 mL of DCE was added dropwise. The mixture was stirred 1 h at room temperature. The reaction was poured into 1N HCl and ice, the organics were separated, washed with H2O, 1N NaOH, H2O, brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue was recrystallized from EtOAc/EtOH to give 116.2 g of solid. mp 173°-176° C. Mass spectrum (Cl-CH4) m/z 307 (M+1). NMR (Me2SO-d6)δ 8.4 (d, 2 H); 8.2 (s,1 H); 8.0 (d, 2 H); 7.1 (s, 1 H); 4.8 (s, 2 H); 4.0 (s, 3 H). Anal calcd for C14H11CIN2O4 : Calcd: C, 54.83; H, 3.61; N, 9.13. Found: C, 55.11;H, 3.70; N, 9.10.

Provenance & Evidence