Potassium Hydroxide → 5,7-Dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyl indeno[5,6-d]imidazol-6(1H)-one oxime

Participants

Reaction Steps

A solution of 560 mg of potassium hydroxide in 1.4 ml of methanol and a solution of 700 mg of hydroxylamine hydrochloride in 3.6 ml of methanol were mixed together at 40°, whereupon the mixture was stirred for 30 minutes and 300 mg of 5,7-dihydro-2[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one were added thereto. The reaction mixture was stirred at 40° under argon for 3 days and then concentrated and treated with methylene chloride/water. The methylene chloride solution was separated, dried, filtered and evaporated. The residue was chromatographed twice on silica gel with methylene chloride/methanol (9:1), the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. 5,7-Dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyl indeno[5,6-d]imidazol-6(1H)-one oxime was obtained. After recrystallization from ethyl acetate the product melts at 160° with decomposition.

Provenance & Evidence