1-Methylpyrrole → HCID 18519867, compound

Participants

Reaction Steps

N-Methylpyrrole (19.5 g, 0.24 mole) and 2-napthalenoyl chloride (50.0 g, 0.26 mole) 300 mL of dry toluene were heated under reflux overnight with a nitrogen stream bubbling through the reaction mixture. Another 10 mL of N-methylpyrrole was added to the reaction mixture and the reflux was continued for another 38 hr. 100 mL of 20% aqueous 3-(dimethylamino)propylamine was added and stirred for 30 minutes. Et2O/THF was added and the organics were separated off, washed with 1 N HCl, NaHCO3, water, brine and dried (MgSO4). The solvent was evaporated in vacuo to give 51 g (90%) of (2-naphthalenyl)(1-methyl-1H-pyrrol-2-yl)-methanone. mp 108-110° C. CIMS m/z236 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.35 (Ar, 1H); 8.0-7.9 (Ar, 4H); 7.6-7.5 (Ar, 2H); 6.95 (Ar, 1H); 6.8 (Ar, 1H); 6.2 (Ar, 1H); 4.1 (s, 3H).

Provenance & Evidence