Hydrochloric Acid → HCID 58934756, compound

Participants

Reaction Steps

Ethyl 6,8-dibromo-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (732.0 mg, 1.70 mmol) was suspended in methanol-tetrahydrofuran-water (5 mL, 7:2:1). Lithium hydroxide (214 mg, 5.108 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 (50 mL) was added, and the solution was washed with water (2×50 mL), saturated ammonium chloride (2×50 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 6,8-dibromo-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid (633.0 mg, 1.52 mmol) as a yellow solid (89% yield): 1H NMR (CD3OD3, 300 MHz)7.07 (s, 1H), 7.57 (d, 1H, J=2.0 Hz), 7.39 (d, 1H, J=2.0 Hz), 5.26 (m, 1H). Anal. Calcd for C11H6Br2F3NO3: C, 32.95; H, 1.51; N, 3.49. Found: C, 32.88; H, 1.51; N, 3.46.

Provenance & Evidence