Hydrochloric Acid → 7-Quinolinol, 1,2,3,4-tetrahydro-

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Reaction Steps

PtO2 (528 mg, 2.33 mmol) was added to a dry flask. Ethanol (70 mL), tetrahydrofuran (70 mL), and hydrogen chloride (7.6 mL, 2N) were added after the flask was flushed with argon. Quinolin-7-ol (1000 mg, 6.89 mmol) was added into the flask under argon atmosphere. The solution was degassed and flashed with argon. Hydrogen gas was introduced to the flask by a balloon. The mixture was stirred at H2 atmosphere at room temperature overnight. The mixture was filtered and the filtrate was concentrated. The resulting residue was purified by MPLC (biotage) to afford 730 mg (71%) of the title compound. 1H-NMR (CDCl3) δ 6.77 (d, J=7.6 Hz, 1H), 6.10 (dd, J=8.0 Hz, 2.8 Hz, 1H), 5.95 (d, J=2.4 Hz, 1H), 3.24 (t, J=5.9 Hz, 2H), 2.66 (t, J=5.9 Hz, 2H), 2.44 (m, 2H); Rf=0.74, 50% ethyl acetate-hexane.

Provenance & Evidence