1,10-Phenanthroline → HCID 69146517, compound

Participants

Reaction Steps

A mixture of methyl 4-iodobenzoate (5.24 g, 20.0 mmol), caprolactam (2.26 g, 20.0 mmol), K2CO3 (3.58 g, mmol), CuI (1.53 g, mmol), and 1,10-phenantroline (1.45 g, 35 mmol, 3.3 eq) was heated at 120–125° C. for 15 h. To the cooled mixture was added EtOAc/H2O. The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash chromatography (hexanes:EtOAc=1:1 to 0:1) to give pure 4-(2-oxo-azepan-1-yl)-benzoic acid methyl ester as a white solid (2.56 g, yield: 51.8%). 1H NMR (DMSO-d6) δ 8.01 (d, J=8.6 Hz, 2H), 7.31 (d, J=8.6 Hz, 2H), 3.87 (s, 3H), 3.76 (m, 2H), 2.68 (m, 2H), 1.79 (m, 4H) ppm. LC-MS (ESI) 248.28 (M+H), tR=2.69 min (10–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run).

Provenance & Evidence