Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-5-nitro-4-oxoquinoline-3-carboxylate → Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylate

HRID 561148Notes

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[CH3:27])[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]([CH3:27])[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-2-methyl-5-nitro-4-oxoquinoline-3-carboxylate (200 mg, 0.523 mmol) and iron powder (175 mg, 3.14 mmol) in AcOH (5 mL) was stirred at 90° C. for 2 h. After the reaction mixture was concentrated in vacuo, 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-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylate (200 mg, quant.) as a yellow oil.

Workup

concentrationAfter the reaction mixture was concentrated in vacuo
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-8b6bb9afcad74275990c8a03fb6d4764
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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