Ethyl 8-Chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate → Ethyl 5-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 2372081Notes

Reaction equation

HRID 2372081 reaction equation
[Cl:1][C:2]1[C:3]([F:25])=[C:4]([F:24])[C:5]([N+:21]([O-])=O)=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]2=[O:20].[H][H]>C(O)C.O1CCCC1.[Ni].ClCCl>[NH2:21][C:5]1[C:4]([F:24])=[C:3]([F:25])[C:2]([Cl:1])=[C:11]2[C:6]=1[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:10]2[CH:12]1[CH2:13][CH2:14]1

Participants

7

Reactant 2

HCID 14896545Ethyl 8-Chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15052639Ethyl 5-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 86.2%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 21.7 g (58.2 mmol) of ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate in 300 ml of ethanol and 300 ml of tetrahydrofuran was catalytically reduced using 3 g of Raney nickel in a hydrogen atmosphere of 50 psi. After twelve hours the mixture was diluted with dichloromethane and the catalyst was removed by filtration. The filtrate was concentrated to give 17.2 g of the title compound.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ef4977fe36b0486d8c200e953b1a25e0
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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