HCID 66617790, compound → HCID 66617677, compound

Participants

Reaction Steps

To solution of 400 mg 2-(2-cyclopropyl)-6-nitro-3-oxo-4-(p-methoxybenzyl)-benz[1,4]oxazine in acetonitrile/water (50 mL) was added 2.5 eq of ceric ammonium nitrate. The reaction mixture was stirred at ambient temperature for 18 hour, filtered, concentrated and the resulting residue partitioned between bicarbonate solution and EtOAc. The aqueous phase was extracted with EtOAc and the combined organics washed with water, brine and then dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography (hexanes/EtOAc) to yield 250 mg of the desired product 2-(2-cyclopropyl)-6-nitro-3-oxo-4H-benz[1,4]oxazine. MS (m/e): 341 (MH+).

Provenance & Evidence