HCID 70453253, compound → HCID 13560807, compound

Participants

Reaction Conditions

Reaction Steps

2.33 grams of 80 percent pyridinium bromide perbromide (1.46 millimoles) was added to a solution of 500 milligrams (1.51 millimoles) of bis(2-hydroxyethyl) 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate in 400 milliliters of ethylene dichloride and 1.6 milliliters of pyridine. The resulting mixture was stirred at 0° C. for 1 hour and then heated at reflux temperature for 2 hours. Thereafter, the mixture was cooled to room temperature, the resulting solution washed with 2N hydrochloric acid, sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered, and the filtrate subjected to reduced pressure to vaporize the solvent and to recover as residue a semi-crystalline solid. The solid was not crystallizable from acetonitrile. The acetonitrile was vaporized to obtain an orange oil which on trituration with ethyl acetate produced crystals. The crystals, after recrystallization twice from ethyl acetate, had a melting point of 185°-186° C. 1H NMR and elemental analyses showed the product to have ethyl acetate solvate of crystallization. Elemental analyses were as follows:

Provenance & Evidence