HCID 23431782, compound → Ethyl 5-amino-1-cyclopropyl-7-chloro-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 47899Notes

Reaction equation

HRID 47899 reaction equation
C([NH:8][C:9]1[C:18]([F:19])=[C:17]([Cl:20])[C:16]([F:21])=[C:15]2[C:10]=1[C:11](=[O:30])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][N:14]2[CH:22]1[CH2:24][CH2:23]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.C(O)C.[Pd]>[NH2:8][C:9]1[C:18]([F:19])=[C:17]([Cl:20])[C:16]([F:21])=[C:15]2[C:10]=1[C:11](=[O:30])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][N:14]2[CH:22]1[CH2:23][CH2:24]1

Participants

6

Reactant 2

HCID 23431782HCID 23431782, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23431781Ethyl 5-amino-1-cyclopropyl-7-chloro-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 83.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 48.0 g of ethyl 5-benzylamino-1-cyclopropyl-7-chloro-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.111 mol) dissolved in a mixture of 200 ml of acetic acid and ethanol was added 0.5 g of 5% Pd/C catalyst. Hydrogen gas was introduced at room temperature. The reaction was monitored with TLC and carried out for around 3 hours. Precipitates collected by filtration were dissolved in chloroform and filtered to remove the catalyst. After removing the solvent by evaporation, the residue was recrystallized from a mixture of chloroform and ethanol to give 32.0 g of ethyl 5-amino-1-cyclopropyl-7-chloro-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.093 mol) in 83.9% yield.

Workup

  1. customPrecipitates
  2. filtrationcollected by filtration
  3. dissolutionwere dissolved in chloroform
  4. filtrationfiltered
  5. customto remove the catalyst
  6. customAfter removing the solvent
  7. customby evaporation
  8. customthe residue was recrystallized from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-413e57f0be8f4c62a00cb5ffebcf0641
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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