Monobenzone → 4-(4-(benzyloxy)phenoxy)-N-methylpicolinamide

Participants

Reaction Steps

To a stirred RT slurry of NaH (2.24 g of 60% oil dispersion, 55.9 mmol) in 40 mL DMF was added 4-benzyloxyphenol (11.2 g, 55.9 mmol). The mixture was stirred for 10 min before adding 4-chloro-pyridine-2-carboxylic acid methylamide (Example 2 Step A, 3.18 g, 18.6 mmol). The reaction was stirred at RT for 5 min, then at 75° C. for 2 h, and finally at 85° C. for 6 h. The reaction was cooled to RT, quenched with saturated aqueous NaHCO3, then diluted with Et2O and 6 N NaOH. The layers were separated, and the organic layer was washed twice with 6 N NaOH, once with brine, dried over Na2SO4, filtered, and concentrated in vacuo, to yield the title compound as a light salmon-colored solid. MS (MH+)=335.1; MW Calc'd 334.38 for C20H18N2O3.

Provenance & Evidence