Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate → Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 620879Notes

Reaction equation

HRID 620879 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:17]([O-])=O)[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[H][H]>[Ni].C(O)C>[NH2:17][C:9]1[C:10]([F:16])=[C:11]([F:15])[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14006857Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14127986Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 34.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1.9 g (5.3 mmoles) of ethyl 1-cyclopropyl-5-nitro-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 0.5 g of Raney nickel and 100 ml of ethanol was shaken in a hydrogen atmosphere at pressures of 42.5-50 psi and temperatures of 24°-26.5° C. for ten hours. The mixture was filtered through Celite and some insoluble product was dissolved in tetrahydrofuran with filtration. The combined filtrates were evaporated in vacuo and the residue was chromatographed on silica gel to give 600 mg of the title compound, mp 223°-225° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. dissolutionsome insoluble product was dissolved in tetrahydrofuran with filtration
  3. customThe combined filtrates were evaporated in vacuo
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1527fb2132fc423fa8c33b81654f4918
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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