Hydrochloric Acid → N-(2-cyanoethyl)glycine

Participants

Reaction Conditions

Reaction Steps

Glycine (5 g, 67 mmol) was suspended in water (10 cm3) and TMAH (25% in water, 24.3 g, 67 mmol) was added slowly, keeping the temperature at <30° C. with an ice-bath. The mixture was then cooled to 10° C. and acrylonitrile (3.89 g, 73 mmol) was added. The mixture was stirred overnight, and allowed to warm to room temperature slowly. The mixture was then neutralized with HCl (6M, 11.1 cm3), concentrated to 15 cm3 and diluted to 100 cm3 with EtOH. The solid precipitated was collected by filtration, dissolved in hot water (6 cm3) and reprecipitated with EtOH (13 cm3) to give 2-(2-cyanoethylamino)acetic acid (5.94 g, 69.6%) as a white solid, mp 192° C. (lit mp 190-191° C.).

Provenance & Evidence