Sodium Hydroxide → 3-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

2.80 Grams of sodium hydroxide was dissolved in 15 ml of water and 200 ml of methanol, then to this solution was added 10.63 g of 2-mercapto-5-methoxybenzimidazole and the reaction mixture was heated with stirring at 55° C. for 30 minutes. Next, 13.33 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline was added to the reaction mixture, then the whole reaction mixture was stirred under heating for 2.5 hours. After the reaction was completed, the solvent was removed by evaporation under reduced pressure, then to the residued thus obtained was added a small amount of 30% sodium hydroxide aqueous solution, and extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then the extract was dried with anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to obtain 18.80 g of 3-methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline as in the form of colorless caramel-like substance.

Provenance & Evidence