Chloroacetic Acid → (2-Imino-2H-pyridin-1-yl)-acetic acid

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottom flask, 2-chloroacetic acid (10 g, 106 mmol) in water (16.3 mL) was treated with triethylamine (16.67 mL, 120 mmol) dropwise over about 6 minutes. After stirring the reaction at ambient temperature for 10 minutes, 2-aminopyridine (11.76 g, 125 mmol) was added and the mixture was heated at 90° C. for 5 hours. The reaction mixture was cooled to ambient temperature and diluted with ethanol (11 mL). The resulting suspension was stirred in an ice bath for 1 hour and filtered. The solid collected was washed with about 30 mL cold ethanol and dried under vacuum to a constant weight to provide the title compound. MS (DCI+) m/e 152.9 (M+H)+.

Provenance & Evidence