O-Xylene → HCID 10708148, compound

Participants

Reaction Steps

A warmed (40° C.) solution of the above azidocinnamate (5.08 g, 16.3 mmol) in xylenes (140 mL) was added to boiling xylenes (60 mL) over 1 h. After a further 15 min at reflux, most of the xylene was removed by distillation. The precipitate that formed in the cooled residue was isolated by filtration, washed with CHCl3 and hexanes, and crystallized from MeOH to give methyl 6-(2-chloroethoxy)-5-methoxyindole-2-carboxylate (2.423 g, 52%) as fluffy white needles, mp 164-166° C. (sublimes 110° C.). 1H NMR [(CD3)2SO] δ 11.65 (br s, 1 H, NH), 7.13 (s, 1 H, H-4), 7.03 (d, J=1.6 Hz, 1 H, H-3), 6.91 (s, 1 H, H-7), 4.24 (t, J=5.2 H, 2 H, OCH2), 3.98 (t, J=5.2 H, 2 H, CH2Cl), 3.84 3.78 (2×s, 3 H each, OCH3); 13C NMR δ 161.5 (CO2), 147.8, 145.8, 132.4, 125.5, 120.3 (C-2, 3a, 5, 6, 7a), 107.8 (C-3), 103.0 (C-4), 96.3 (C-7), 68.9 (OCH2), 55.7 (OCH3), 51.4 (CO2CH3), 42.9 (CH2Cl).

Provenance & Evidence