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

HRID 561153Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-])=O)[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:5]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:3][CH2:2]1>CC(O)=O.[Fe]>[NH2:18][C:9]1[C:10]([F:17])=[C:11]([F:16])[C:12]([O:14][CH3:15])=[C:13]2[C:8]=1[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:5]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

concentrationAfter the reaction mixture was concentrated in vacuo, water
additionwas added
extractionthe crude product was extracted with EtOAc
washwashed with saturated aq. NaHCO3 and brine
dry with materialdried over MgSO4
customThe solvent was removed in vacuo
customthe residue was dried

Sources & evidence

ORD record: ord-6066176957904da8aa7a3b8384ac0277
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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