Hydrochloric Acid → HCID 67164698, compound

Participants

Reaction Steps

A round bottom flask with magnetic stirrer was charged with cis-2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (980 mg, 2.60 mmol) in tetrahydrofuran (10.0 mL). To the reaction was added a solution of lithium hydroxide (179 mg, 7.47 mmol) in water (10 mL), followed by methanol (10 mL). The reaction was stirred at room temperature for 18-20 hours under an argon atmosphere. The reaction was transferred to a separatory funnel and the pH adjusted to 2 via addition of 1N hydrochloric acid. The mixture was extracted with ethyl acetate (3×35 mL) and the combined extractions were washed with brine (1×50 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to yield 2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (mixture of cis and trans isomers) as an off-white solid (912 mg, 97%). The mixture was used without purification in subsequent reactions.

Provenance & Evidence