Methanol → HCID 11516399, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-(5-ethyl-2-pyridyl)ethoxy)phenylammonium bromide (52.8 mmol) in hydrobromic acid (prepared by hydrolyzing 4-(2-(5-ethyl-2-pyridyl)ethoxy)acetanilide according to Example 1c) 25 ml of 48% hydrobromic acid, 50 ml of methanol, 100 ml of acetone are added and the mixture is cooled to 0° C. A solution of sodium nitrite (4.5 g) in water (10 ml) is added dropwise to the mixture at 0 to 5° C. The mixture is mixed at 5° C. for another 20 mins, then acrylonitrile (16.8 ml) is added and the temperature is elevated to 38° C. Cuprous oxide (0.5 g) is added in small portions. The mixture is agitated until release of nitrogen stops, then concentrated under reduced pressure, the concentrate is alkalified by adding an aqueous ammonia solution and extracted with ethyl acetate. The ethylacetate layer is washed with water and dried over sodium sulfate. Evaporating the solvent gives the nitrile of 2-bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]-propionic acid as crude oil (18.7 g, 99% of theory).

Provenance & Evidence