p-Anisoyl chloride → cis-1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester

Participants

Reaction Steps

A round bottom flask with magnetic stirrer was charged with cis-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (5.42 g, 26 mmol) in dichloromethane (100 mL) under an argon atmosphere at room temperature. To the reaction was added N,N-diisopropylethylamine (11.8 mL, 68 mmol), followed by p-anisoyl chloride (6.31 g, 37 mmol). The reaction was stirred at room temperature for 18-20 hours and poured into saturated sodium bicarbonate (1000 mL), diluted with dichloromethane (50 mL), and shaken vigorously. The resulting organic layer was separated, washed with brine (1×100 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford an oily residue. Diethyl ether (50 mL) was added to the residue and the resulting white solid was collected via suction filtration to afford cis-1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (6.94 g, 78%).

Provenance & Evidence