Sodium Hydroxide → 2-(3-((1-Ethylpyrrolidin-2-yl)methylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

A mixture of methyl 2-(3-((1-ethylpyrrolidin-2-yl)methylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (44 mg, 0.1 mmol) in methanol (1.6 mL) and 1 M sodium hydroxide aqueous solution (1.27 mL, 1.27 mmol) was heated to reflux for 30 min, LC-MS showed the reaction was complete and only the desired product formed. The solvent was concentrate in vacuo and the residue was dissolved in water and acidified with 1 M hydrochloric acid solution. The off-white precipitated solid was collected by filtration to afford mg of 2-(3-((1-ethylpyrrolidin-2-yl)methylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid was a white solid. Yield: 58.7%. MS (ESI+APCI) M+1=436.3.

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