Formaldehyde → 3-(Dimethylaminomethyl)-7-azaindole

Participants

Reaction Steps

A mixture of 1H-pyrrolo[2,3-b]pyridine (59 g; 0.5 mol), dimethylamine hydrochloride (44.83 g; 0.55 mol) and paraformaldehyde (16.5 g; 0.55 mol) in n-butanol (700 mL) was heated at reflux for 20 minutes. The mixture was cooled to ambient temperature. The precipitated solid was collected by filtration and dried. The solid was then dissolved in water (800 mL), a few drops of HCl was added for complete solution. The aqueous solution was washed with diethyl ether. Solid potassium carbonate was then added to the aqueous phase until basic. The precipitated solid was collected, washed with water and dried to give 43.5 g (50% yield) of the title compound as an off-white solid, m.p. 161°-162° C. Anal. Calcd. for C10H13N3 : C, 68.54; H, 7.48; N, 23.95. Found: C, 68.28; H, 7.75; N, 23.99. Mass spectrum (DEI; M+) m/z 175. 1H-NMR (DMSO-d6 ; 400 MHz) δ 12.45 (br s, 1H), 8.14 (dd, 1H), 7.97 (dd, 1H), 7.32 (s, 1H), 7.01 (q, 1H), 3.51 (s, 2H), and 2.12 ppm (s, 6H).

Provenance & Evidence