Diethylamine → HCID 18519862, compound

Participants

Reaction Steps

A solution of 3.19 g (0.0094 mole) of 2-chloro-1-[5-(4-chlorobenzoyl)-1-ethylmethoxy-1H-pyrrol-3-yl]ethanone, 75 mL of 2-PrOH, and 2.9 mL (0.028 mole) of diethylamine was heated under reflux for 4 h. The solvent was evaporated in vacuo. The residue was partitioned between Et2O and 2N NaOH. The organics were washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue chromatographed on silica gel (9:1 CH2Cl2: MeOH). The oil was treated with ethereal HCl and the resulting solid recrystallized from 2-PrOH to give 0.9 g (26%) of Compound 9. mp 149-151° C. CIMS m/z 377 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.2 (Ar, 1H); 7.8 (Ar, 2H); 7.7 (Ar, 2H); 7.2 (Ar, 1H); 4.7 (m, 2H); 4.6 (t, 2H); 3.65 (t, 2H); 3.2 (m, 3H); 3.15 (m, 4H); 1.2 (t, 6H). Calc'd for: C20H25CIN2O3.HCl: C, 5.12; H, 634; N, 6.78. Found: C, 58.29; H, 6.31; N, 6.55.

Provenance & Evidence