Sodium Iodide → HCID 86753922, compound

Participants

Reaction Steps

To a mixture of (±)-7-[1-[(chloroacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (100 mg, 0.26 mmol) in acetone (10 mL) was added sodium iodide (150 mg, 1.0 mmol), and the resulting solution was heated at reflux for 1 h. Upon cooling, a solid precipitate appeared. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and H2O. The organic extract was washed with H2O (3×), dried over sodium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (CDCl3) d 8.35 (s, 1H), 8.22 (d, J=8.2 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.81 (m, 1H), 7.66 (m, 1H), 7.38 (s, 1H), 5.91 (dd, J=7.9, 6.0 Hz, 1H), 5.26 (two s, 2H), 3.84 (d, J=10.1 Hz, 1H), 3.75 (d, J=10.1 Hz, 1H), 2.36 (s, 3H), 2.10-1.83 (m, 2H), 1.03 (t, J=7.4 Hz, 3H). Anal. Calcd for C21H19IN2O3.1/2 H2O: C, 52.19; H, 4.17; N, 5.80. Found: C, 52.16; H, 4.05; N, 5.39.

Provenance & Evidence