Dimethylacetamide → 1-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (80 mg, 0.35 mmol), and lithium phenoxide (1 mL, 1.04 mmol, 1M solution in THF) were suspended in DMAC (2 mL), and stirred for 4 h at 100° C. The reaction mixture was cooled to room temperature, and diluted with H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 137 (22 mg, 22% yield) as a tan solid. LC-MS (M+H=289, obsd.=289). 1H NMR (400 MHz, d6-DMSO): δ 12.12 (s, 1H), 9.08 (d, 1H), 8.42 (dd, 1H), 8.28 (d, 1H), 7.88 (td, 1H), 7.70 (t, 1H), 7.55 (m, 2H), 7.35 (m, 3H), 6.55 (d, 1H).

Provenance & Evidence