Methyl iodide → Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (0.33 g, 1.12 mmol) was combined with KOH (0.31 g, 5.6 mmol) and iodomethane (1.3 g, 8.96 mmol) in ethylene glycol dimethyl ether (5.6 mL) and stirred at 90° C. for 16 h. The inorganic solid was filtered and the filtrate evaporated to give ethyl-5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (0.37 g) as an orange oil in near quantitative yield. 1H NMR (CDCl3, 300 MHz) δ 7.74 (d, 1H, J=7.7 Hz), 7.67 (d, 1H, J=7.7 Hz), 7.12 (t, 1H, J=8.0 Hz), 4.70 (s, 2H), 4.22 (q, 2H, J=7.0 Hz), 3.91 (br. s, 2H), 3.62 (s, 3H), 2.84 (t, 2H, J=5.5 Hz), 1.30 (t, 3H, J=7.0 Hz) ppm.

Provenance & Evidence