Dimethylformamide → HCID 14366447, compound

Participants

Reaction Steps

A mixture of quindoline-11-carboxylic acid (2.6 g, 10 mmol) from Example 1, DMF (25 mL), KOH (2.24 g, 40 mmol), BaO (6.27 g, 40 mmol) and methyl iodide (9.7 mL, 130 mmol) was stirred at room temperature for 48 hours, then partitioned between benzene (60 mL) and water (100 mL). The benzene layer was washed with water (2×60 mL), dried and concentrated. The residue was recrystallized from hexane to afford 1.14 g (39.3%) of the title compound as light yellow crystals, mp 127° C.; 1H NMR (CDCl3) δ 8.49 (d, J=8.0, 1H), 8.31 (d, J=8.0, 1H), 7.95 (d, J=8.4, 1H), 7.68-7.55 (m, 3H), 7.42 (d, J=8.0, 1H), 7.37 (t, J=7.2, 1H), 4.14 (s, 3H), 3.79 (s, 3H); 13C NMR (CDCl3) δ 167.98, 146.93, 145.64, 143.25, 130.27, 129.66, 126.52, 123.55, 122.92, 122.02, 121.28, 120.42, 115.77, 108.70, 52.71, 30.75; MS (EI, M/z) 290.1 (M+)

Provenance & Evidence