Methanol → HCID 68549576, compound

Participants

Reaction Steps

2-[(2-Aminoquinolin-3-yl)methyl]-3-methoxyphenol (40 mg, 0.14 mmol), triphenylphosphine (56 mg, 0.21 mmol) and methanol (7 μL, 0.22 mmol) were placed in THF (2 mL) at 10° C. and then mixed slowly with azodicarboxylate diisopropyl ester (44 mg, 0.22 mmol) in THF (1 mL). Then the mixture was stirred for 12 hours at room temperature. The batch was mixed with water and extracted with ethyl acetate. The combined organic phases were washed with water, dried (sodium sulfate) and concentrated. The crude product was purified chromatographically (silica gel, dichloromethane, methanol). To remove traces of triphenylphosphine oxide, the slightly contaminated product was dissolved in diethyl ether and extracted with 2N aqueous hydrochloric acid. The aqueous phase was alkalized with dilute sodium hydroxide solution and extracted with dichloromethane. The combined dichloromethane extracts were washed with water until neutral, dried (sodium sulfate) and concentrated (yield: 5 mg, 9%).

Provenance & Evidence