Hydrogen Peroxide → HCID 66997518, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (22 g, 58 mmol) was dissolved in 500 mL glacial acetic acid and H2O2 (30% by weight in water, 65.8 mL) was added. The reaction was warmed to 100° C. and aged for four hours at which time LCMS showed the reaction done. The solution was cooled in an ice bath to 25° C. and treated with saturated Na2SO3 solution, keeping the temperature below 40° C. When starch paper test showed no peroxides present, the solution was concentrated by ⅓, the pH was adjusted to ˜3 with aqueous HCl and the solution extracted with CH2Cl2 several times. The organic layers were dried over Na2SO4, filtered and evaporated to give product as an oil.

Provenance & Evidence