Trifluoroacetic acid → 7-(3-Hydroxypropyl)-8-benzyloxy-9-methoxy-naphtho[2,3-c]phenanthridine

Participants

Reaction Conditions

Reaction Steps

8-Benzyloxy-9-methoxy-naphtho[2,3-c]phenanthridine (231 mg, 0.56 mmol) was suspended in acetonitrile (80 mL), and trifluoroacetic acid (43 μL, 0.56 mmol), 3-bromo-1-propanol (51 μL, 0.56 mmol) and tris(trimethylsilyl)silane (346 μL, 1.12 mmol) were added to the suspension. The mixture was stirred at 80° C. on an oil bath. After the suspended matter was dissolved, azobis(isobutyronitrile) (184 mg, 1.12 mmol) was added to the solution followed by heating under reflux. An hour later, the reaction mixture was cooled to room temperature. Saturated sodium hydrogencarbonate aqueous solution (50 mL) was added to the residue followed by extraction with methylene chloride. After the organic layer was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off in vacuo. The residue was passed through a silica gel column (eluted with 1% methanol-methylene chloride). The main fractions were collected and the solvent was distilled off in vacuo. The residue was dissolved in toluene (3 mL) and activated manganese dioxide (100 mg) was added to the solution. The mixture was stirred at room temperature for 90 minutes. Manganese dioxide was filtered off and the filtrate was concentrated in vacuo to provide crude 7-(3-hydroxypropyl)-8-benzyloxy-9-methoxy-naphtho[2,3-c]phenanthridine (83 mg) as brown dry mass.

Provenance & Evidence