Hydrochloric Acid → HCID 86658607, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-methoxycarbonyl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2 g, 5.45 mmol) in methanol (20 mL) and tetrahydrofuran (50 mL), 30% sodium hydroxide in water (20 mL) was stirred at 50° C. for 24 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 2-(3-carbonyl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (500 mg, 28%) as a white solid: LC/MS m/e calcd for C19H19NO4 (M+H)+: 326.27, observed: 326.0.

Provenance & Evidence