4-(Benzylamino)phenol → N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 4-(benzylamino)phenol (78 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 136 (8 mg, 20% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 12.06 (s, 1H), 9.11 (d, 1H), 8.42 (dd, 1H), 8.26 (d, 1H), 7.82 (d, 1H), 6.99 (d, 2H), 6.70 (m, 3H), 6.48 (d, 1H), 6.42 (s, 2H).

Provenance & Evidence