Methyl iodide → 1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (7.03 g, 39.4 mmol) in dimethylformamide (50 ml) was added potassium carbonate (16.3 g, 118 mmol) and iodomethane (3.7 ml, 59.1 mmol) and the reaction stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was taken up in water (400 ml) and extracted into ether (3×200 ml). The combined ether extracts were washed with brine (100 ml), dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 20-40% EtOAc/40-60° C. petroleum ether gave the title compound as an orange solid (5.35 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.42 (dd, 1H), 7.33 (d, 1H), 7.01 (d, 1H), 3.31 (m, 2H), 2.96 (s, 3H), 2.80 (t, 2H), 1.99 (m, 2H).

Provenance & Evidence