HCID 59002963, compound → Ethyl 5-amino-1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.0 g, 4.78 mmol) and iron powder (2.67 g, 47.8 mmol) in AcOH (20 mL) was stirred e at 90° C. for 5 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The residue was diluted with water and basified with aq. NaOH. The mixture was filtrated over celite and washed with CH2Cl2. The resulting solution was extracted with CH2Cl2. The organic layer washed with water, brine, and then dried. The solvent was removed and the resulting solid washed with EtOH, dried to yield ethyl 5-amino-1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (1.12 g, 60%) as a yellow solid. M.p. 134-135° C.

Provenance & Evidence