ethyl quinoline-3-carboxylate → Ethyl 1,2,3,4-tetrahydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl quinoline-3-carboxylate (Aldrich, 15.44 g, 76.7 mmol) was added to a mixture of ethanol (150 mL) and 10% palladium on carbon (3.0 g) in a Parr shaker. The glass reactor was sealed and flushed with nitrogen, and pressurized with hydrogen (60 psi). The mixture was shaken at 50° C. for 52 hours. The solids were filtered, rinsed with methanol, concentrate under reduced pressure, and chromatographed on silica gel eluting with 5-40% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.19 (t, J=7.12 Hz, 3H), 2.83 (m, 3H), 3.17 (m, 1H), 3.39 (m, 1H), 4.09 (q, J=7.12 Hz, 2H), 5.74 (s, 1H), 6.44 (m, 2H), 6.86 (m, 2H). MS (DCI) m/z 206.10 (M+H)+.

Provenance & Evidence