3-(Trifluoromethyl)phenol → 5-Nitro-1-(3-(trifluoromethyl)phenoxy)isoquinoline

Participants

Reaction Steps

To a solution of 1-chloro-5-nitroisoquinoline (Step-1, Intermediate-1, 200 mg, 0.96 mmol) in CH3CN (2 mL) were added 3-(trifluoromethyl)phenol (233 mg, 1.4 mmol) and K2CO3 (265 mg, 1.92 mmol). The reaction mass was heated at reflux for 5 h and it was diluted with water and extracted with chloroform. The organic layer was separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 1.2 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.82 (d, J=8.4 Hz, 1H), 8.58 (d, J=7.8 Hz, 1H), 8.17 (s, 2H), 7.76 (t, J=8.4 Hz, 1H), 7.61-7.47 (m, 4H); MS (m/z): 335.12 (M+H)+.

Provenance & Evidence