Formaldehyde → 3-(Dimethylaminomethyl)-7-azaindole

Participants

Reaction Steps

7-azaindole (5.0 g, 17 mmole), dimethylammonium chloride (3.76 g), and paraformaldehyde (1.40 g) were dissolved in n-butanol (30 mL). The reaction was refluxed for 1 hour where upon cooling to room temperature fluffy white needles crystalized out. These were filtered and washed with butanol (10 mL). The solid was dried in vacuo to a white crystalline solid massing 6.1 g. A portion of this material (2.0 g) was converted to the free base by dissolving in 20 mL water. Upon the addition of ammonium hydroxide (aqueous, 30%) (2 mL) a white precipitate formed, was filtered, washed with water (5 mL), and dried in vacuo to yield 3-(N,N-dimethylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (2.0 g, 27% yield). δH (300 MHz CDCl3) 2.27 (6H, s), 3.61 (2H, s), 7.09 (1H, dd, J=4.5 and 8.0), 7.28 (1H, s), 8.04 (1H, dd, J=1.2 and 8.1), 8.32 (1H, dd, J=1.2 and 4.7), ESMS 176 (MH+)

Provenance & Evidence