Chloroacetic Acid → 1-(Carboxymethyl)pyridinium chloride

To a solution of pyridine (4.0 g) in ethyl acetate (10 mL) was added chloroacetic acid (4.7 g) at room temperature, and the mixture was heated under reflux overnight. After the reaction mixture was cooled to room temperature, the precipitated solid was collected by filtration, and dried under reduced pressure to give 1-carboxymethyl pyridinium chloride (5.7 g). To a solution of the obtained compound (5.7 g) in toluene (300 mL) were added acrylonitrile (8.7 g), manganese dioxide (16.4 g) and triethylamine (4.0 g), and the mixture was stirred at 100° C. for 5 hours. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.8 g).

1. temperaturethe mixture was heated
2. temperatureunder reflux overnight
3. filtrationthe precipitated solid was collected by filtration
4. customdried under reduced pressure

ORD record

ord-d993914943f94a36999abc686317309c

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748452B2