Methyl quinoline-5-carboxylate → Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

Participants

Reaction Steps

Methyl quinoline-5-carboxylate (3.67 g, 19.61 mmol) was dissolved in TFA (60 ml) and added platinum oxide (0.49 g, 2.16 mmol) then hydrogenated at room temperature overnight. Filtered off the catalyst and evaporated to dryness. The residue was chromatographed through a 120 g ISCO Redi-sep column and eluted with 5% of (10% NH4OH in MeOH) in DCM to yield methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate 1H-NMR (600 MHz, CDCl3): δ ppm 8.42 (d, J=3.7 Hz, 1H), 7.485 (d, J=7.7 Hz, 1H), 7.06-7.08 (m, 1H), 3.82 (t, J=5.6 Hz, 1H), 3.72 (d, J=3.2 Hz, 3H), 3.02-2.93 (m, 1H), 2.88-2.93 (m, 1H), 2.16-2.20 (m, 1H), 1.97-2.05 (m, 2H), 1.85-1.90 (m, 1H); LC-MS: M+1=192.

Provenance & Evidence