Hydrochloric Acid → HCID 86680975, compound

Participants

Reaction Conditions

Reaction Steps

In a 25-mL flask under argon, 7-methoxy-3-(4-methoxyphenyl)-4-nitroisoquinoline-1(2H)-one (compound D5, 150 mg, 0.46 mmol) is dissolved in 5 mL of DMF. Potassium carbonate (317 mg, 2.3 mmol) is then added. After stirring for 30 minutes, 2-bromoethanol (329 μl, 4.6 mmol) is added. Stirring is maintained for 24 hours at 50° C. Once returned to ambient temperature, the medium is neutralized with 20 mL of a 1N hydrochloric acid solution then extracted with 3×10 mL of ethyl acetate. The organic phases are washed with 3×10 ml of H2O, dried over MgSO4 and concentrated under vacuum. The residue obtained is chromatographed on a silica gel column using the cyclohexane-ethyl acetate mixture (60/40) as eluent in order to produce the expected 2-(2-hydroxyethyl)-7-methoxy-3-(4-methoxyphenyl)-4-nitroisoquinoline-1(2H)-one 68 (73 mg, 43%) in the form of a yellow solid.

Provenance & Evidence