1,10-Phenanthroline → 252752-46-8

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-iodophenylacetate (4.25 g, 15.39 mmol) was dissolved in DMF (25 mL). BOC-carbazate (2.44 g, 18.47 mmol), 1,10-phenanthroline (278 mg, 1.54 mmol), copper iodide (147 mg, 0.77 mmol) and cesium carbonate (7.0 g, 21.55 mmol) were added and the mixture heated at 120° C. for 60 min. The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (3×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to leave a brown oil which was purified by flash chromatography on silica gel (elution gradient 0-50% EtOAc in isohexane) to give a colourless oil. The oil was dissolved in 4M HCl Dioxan (20 mL) and stirred at ambient temperature for 3 h giving a thick precipitate. Diethyl ether (100 mL) was added and the precipitate recovered by filtration, washed with ether (2×20 mL) and dried under vacuum to leave methyl 2-(4-hydrazinylphenyl)acetate_hydrochloride as a light brown solid. (1.63 g, 49%)

Provenance & Evidence