Methyl iodide → HCID 44326150, compound

Participants

Reaction Steps

A solution of methyl 10-methylquindoline-11-carboxylate (0.5 g, 1.72 mmol) from Example 13 in methyl iodide (5 mL, 50.3 mmol) was stirred at room temperature for 48 hours. The excess of CH3I was removed in vacuo and the residue was dissolved in MeOH (10 mL). Diethyl ether (30 mL) was added and the precipitate was filtered and washed thoroughly with diethyl ether to afford, after drying, 0.33 g (44.6%) of the title compound as an orange solid, mp 257.0-257.5° C. (decomp.); 1H NMR (DMSO-d6) δ 8.90 (dd, J=2.8, J=9.2, 2H), 8.33 (d, J=8.0, 1H), 8.24 (t, J=6.8, 1H) 8.10 (t, J=5.2, 2H), 8.04 (t, J=8.4, 1H), 7.62 (t, J=8.0, 1H), 5.08 (s, 3H), 4.31 (s, 3H), 3.99 (s, 3H); 13C NMR (DMSO-d6) δ 164.95, 148.00, 140.47, 135.11, 134.96, 132.61, 129.99, 128.74, 126.96, 125.76, 124.86, 122.31, 122.27, 118.72, 113.60, 111.71, 54.67, 41.20, 30.98; MS (LSIMS, m/z) 305 (M+)

Provenance & Evidence