Toluene → Indolizine-1-carbonitrile

Temperature

100 °C

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. filtrationThe reaction mixture was filtered through a Celite pad
2. concentrationthe filtrate was concentrated under reduced pressure
3. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

ORD record

ord-1659b8d64f83437da7632dcb01de3f51

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748452B2