Hydrochloric Acid → HCID 21883652, compound

Participants

Reaction Steps

Ethyl 6-(4-fluorophenyl)-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (189 mg, 0.51 mmol) was suspended in methanol-tetrahydrofuran-water (10 mL, 7:2:1). Lithium hydroxide (42 mg, 0.1.53 mmol) was added, and the mixture was gently heated to reflux for two hours. The reaction was cooled to room temperature and 1 N aqueous hydrochloric acid added until pH=1. The organic solvent was removed in vauco to afford a suspension of a crude yellow solid. Diethyl ether (20 mL) was added, and the solution was washed with water (2×20 mL), saturated ammonium sulfate (2×20 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 6-(4-fluorophenyl)-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid (152 mg, 0.45 mmol) as a yellow solid (88% yield). 1H NMR (CD3OD3, 300 MHz) 7.81 (s, 1H), 7.40-7.56 (m, 4H), 7.10 (t, 1H, J=9.1 Hz), 6.78 (d, 1H, J=8.3 Mz), 5.12 (m, 1H). HRMS m/z 337.0732; calcd 337.0726.

Provenance & Evidence