Water → HCID 21311473, compound

Participants

Reaction Steps

A mixture of 25 grams (0.089 mol) of 2-(2-hydroxy-butyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, 25 grams (0.25 mol) of succinic anhydride and 50 milliliters of pyridine are stirred and heated at 90° for 2.5 hours. The mixture is poured into 100 milliliters of water and 100 milliliters of methylene chloride. The organic layer is separated and washed twice with 100 milliliters of water following which it is treated with anhydrous magnesium sulfate and activated charcoal, filtered through celite and concentrated under vacuum. The residue is dissolved in a mixture of ethanol methylene dichloride and concentrated to about 80 milliliters volume. The precipitate formed (11.4 grams of bis-[2-(2-hydroxy-butyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone] succinate; m.p. 142° ) is removed by filtration. The remaining filtrate is concentrated to a syrup (17 grams) and dissolved in 100 milliliters of diethyl ether. The solution is added dropwise to an ice-coated solution of diethylether saturated with dry ammonia gas. The white solid formed is filtered off, washed with diethyl ether and dissolved in CH2Cl2. The solution is filtered and then treated with petroleum ether yielding 6.0 grams of [2-(2-hydroxybutyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone] succinic acid ester (m.p. 90°-93° )

Provenance & Evidence