Sodium Hydroxide → 2-(4-Fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

A mixture of methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (183 mg, 0.46 mmol), sodium hydroxide (312 mg, 7.8 mmol) in methanol/water (10 mL/4 mL) was heated to reflux for 1.5 h. LC-MS indicated that the starting material was consumed completely. The solvent was removed in vacuo and the residue was acidified with 2M hydrochloric acid solution to Ph=5. The precipitated white solid was collected by filtration and dissolved in acetone, dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give 2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, which was purified by recrystallization from dichloromethane/methanol/Hexant to afford 140 mg of off-white crystal. Yield: 79.3%. LC-MS (M+1)=385.

Provenance & Evidence