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

HRID 561100Notes

Reaction equation

HRID 561100 reaction equation
[CH:1]1([N:6]2[C:15]3[C:10](=[C:11]([N+:20]([O-])=O)[C:12]([F:19])=[C:13]([F:18])[C:14]=3[O:16][CH3:17])[C:9](=[O:23])[C:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.CN(C=O)C.[Pd]>[CH:1]1([N:6]2[C:15]3[C:10](=[C:11]([NH2:20])[C:12]([F:19])=[C:13]([F:18])[C:14]=3[O:16][CH3:17])[C:9](=[O:23])[C:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 59003055Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 66999743Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-5-amino-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

A solution of 16 (6.0 g, 15 mmol) in EtOH-DMF (4:1, v/v, 250 mL) was hydrogenated under atmospheric pressure over 10% Pd/C (600 mg) at room temperature overnight. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo to dryness to yield 17 (5.0 g, 90%) which was used crude in the next step.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-6b90a713d00e4fb5b729b63a6866d860
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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