Dichloromethane → HCID 117667217, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (2.16 g, 6.90 mmol) and NaH2PO4 (2.38 g, 17.2 mmol) in t-butanol and water (1:1 mixture, 300 mL) is heated to 50° C. and NaMnO4 (11.4 g, 32.2 mmol) solution (aq.) is added. The mixture is heated for 2 hrs. The reaction mixture is cooled and solid Na2SO3 is added until the purple color disappears. 50 mL of EtOAc and 50 mL of water are added and the mixture is filtered through diatomaceous earth to remove the black solid. The aqueous layer of the filtrate is separated and extracted with 2×100 mL of EtOAc. The organic layers are combined dried with MgSO4 and concentrated to give the crude product. The product is dissolved into CH2Cl2 and purified via silica chromatography to give 1.09 g 6-bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence