Hydrochloric Acid → HCID 19815937, compound

Participants

Reaction Steps

A solution of 4-(5-formyl-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (1.2 g) and hydroxylamine hydrochloride (0.26 g) in a mixture of N,N-dimethylformamide (5 ml) and pyridine (4 ml) was stirred at ambient temperature for 2.5 hours. To the reaction mixture was added acetic anhydride (5 ml) and the resulting solution was stirred at 80° C. for 1 hour. The mixture was poured into a mixture of water and ethyl acetate and adjusted to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromotography on silica gel. The column was eluted with a mixture of ethyl acetate and tetrahydrofuran (85:15 V/V) and the fraction was evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 4 -(5-cyano-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (0.66 g).

Provenance & Evidence