Sodium Hydroxide → 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid

HRID 561154Notes

Reaction equation

HRID 561154 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27]CC)=[O:26])=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1.[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:7]2[CH:16]1[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59002984Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 590030445-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acidYield 62,953,556%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylate (980 mg, 2.36 nmol) and 1M aq. NaOH (5 mL) in EtOH (15 mL) was stirred at 50° C. for 24 h. After the reaction mixture was concentrated in vacuo, the residue was dissolved in water and 2M HCl was added to pH<3. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1) to yield 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid (574 mg, 63%) as a yellow amorphous solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. addition2M HCl was added to pH<3
  4. extractionThe crude product was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1)

Sources & evidence

ORD record
ord-da13fc96bdc147d3b447094618053b06
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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