Hydrochloric Acid → HCID 53491972, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4′-isopropoxy-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.30 g, 0.68 mmol) in methanol (2 mL) and tetrahydrofuran (15 mL), lithium hydroxide hydrate (0.28 g, 6.8 mmol) in water (1.0 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×50 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-(4′-isopropoxy-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.18 g, 65%) as a white solid which was used for next step without further purification: LC/MS m/e calcd for C27H29NO3 (M+H)+: 416.5, observed: 416.1.

Provenance & Evidence