Pyridine → HCID 58118641, compound

Participants

Reaction Steps

A mixture of lithium iodide (10.3 g, 77.0 mmol), methyl 2-cyano-5,6,7,8-tetrahydroquinoline-6-carboxylate (3.32 g, 15.4 mmol) and pyridine (39 mL, 480 mmol) was divided evenly between two 35 mL vials and the mixtures submitted to microwave irradiation for 4 hr at 130° C. The reactions were combined and concentrated to ˜15 mL. The residue was diluted with water (50 mL) and DCM (200 mL) and 1M citric acid (150 mL) was added until a pH of 4 was attained. The aqueous was extracted with additional DCM (200 mL) and the combined organics was washed with 0.25 M citric acid (150 mL). The citric acid wash was back extracted with DCM (50 mL) and the combined organics were dried ((Na2SO4), filtered and evaporated. The residue was dissolved in DCM (200 mL) and washed with 0.5 M citric acid (50 mL×2). Each citric acid wash was back extracted with DCM (25 mL) and the combined organics dried (Na2SO4), filtered and evaporated to obtain a yellow solid (2.54 g, 82%). m/z=201.2 (M−H)−. 1H NMR (400 MHz, DMSO-d6) δ 12.47 (br s, 1H), 7.80 (d, J=8.1 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 3.12-2.84 (m, 4H), 2.83-2.74 (m, 1H), 2.22-2.13 (m, 1H), 1.94-1.83 (m, 1H).

Provenance & Evidence