Salicylic Acid → HCID 19429159, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 60.3g (0.37 mole) 2,6-dichloro-3-aminopyridine and salicylic acid 61g (0.44 mole) in 300 mL of toluene were heated to reflux for one hour. The reaction mixture was cooled at 90° C. and 34.2 ml (0.47 mole) of thionyl chloride was slowly added. After the addition the reaction mixture was refluxed for 3 hours, then cooled to room temperature. To the reaction mixture was added a solution containing 20g NaOH in 740 mL of H2O. The organic phase was separated and washed with water. The organic phase was treated with charcoal, filtered and the filtrate treated with CO2, the brownish precipitate was filtered off. Recrystallization from isopropyl alcohol gave 63.3g (60.5%) mp 179°-186° C.

Provenance & Evidence