Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate → Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate (1.05 g, 2.36 mmol) and iron powder (793 mg, 14.2 mmol) in AcOH (25 mL) was stirred at 90° C. for 3 h. After the reaction mixture was concentrated in vacuo, water was added and the crude product was extracted with EtOAc, washed with saturated aq. NaHCO3 and brine, dried over MgSO4. The solvent was removed in vacuo and the residue was dried to yield ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate (1.00 g, quant.) as a yellow amorphous solid.

Provenance & Evidence