Isonicotinic Acid → HCID 22923333, compound

Participants

Reaction Steps

219 ml (3.00 mole) of thionyl chloride were added to a solution of 246.2 g (2.00 mole) of isonicotinic acid in 500 ml of 1,2-dichloroethane and the mixture was refluxed for 4 hours. The excess thionyl chloride and the solvent were removed by evaporation at reduced pressure and 392 ml (4.00 mole) of 1,3-difluorobenzene and then, portionwise, 533 g (4.00 mole) of aluminium trichloride were added over the solid residue. Once the exothermal reaction has ended, the mixture was refluxed for 5 hours. it was cooled and poured over a mixture of 3 kg of ice and 1 kg of water, was stirred for 0.5 hours and the phases were separated. The aqueous phase was washed with 1L of methylene chloride, was than basified with 2L of 40% NaOH and extracted with Ch2Cl2 (2 x 1L). The combined organic extracts were dried (MgSO4) and evaporated at reduced pressure to give 179.4 g (41% yield) of the title compound in the form of an ochre coloured oil.

Provenance & Evidence