Iodoethane → 6-Chloro-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34a) (30 mg) and potassium carbonate (60 mg) in N,N-dimethylformamide (0.5 ml) was added iodoethane (25 mg) and the mixture was stirred at 90° C. for 1.5 hrs. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol (100:1) to give 6-chloro-3-ethoxy-5,9-diaza-benzo[c]-fluoren-7-one (18 mg) as a yellow powder. ESI−MS: m/z 311 (MH+); 1H-NMR (CDCl3): δ1.54 (3H, t, J=7 Hz), 4.25 (2H, q, J=7 Hz), 7.39 (1H, dd, J=9 Hz, 2.5 Hz), 7.43 (1H, d, J=2.5 Hz), 8.10 (1H, d, J=5.5 Hz), 8.35 (1H, d, J=9 Hz), 8.95 (1H, d, J,=5.5 Hz), 9.04 (1H, s).

Provenance & Evidence