Methanol → Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

HRID 1458006Notes

Reaction equation

HRID 1458006 reaction equation
[F:1][C:2]1[C:3]([N+:24]([O-])=O)=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[F:12])[N:8]([C@@H:14]1[CH2:16][C@@H:15]1[F:17])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].CO>[Ni].O1CCOCC1>[NH2:24][C:3]1[C:2]([F:1])=[C:11]([F:12])[C:10]([CH3:13])=[C:9]2[C:4]=1[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][N:8]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17]

Participants

5

Reactant 2

HCID 887MethanolHCID 11014105Ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate

Product 1

HCID 11759598Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 3.91 g (37.6 mmol) portion of ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate was suspended in 1 liter of a 1:1 mixture of methanol and 1,4-dioxane. This was mixed with 200 ml of Raney nickel and stirred for 10 minutes at room temperature. After completion of the reaction, the reaction solution was filtered and the resulting filtrate was concentrated. The resulting residue was dissolved in 300 ml of chloroform and filtered through celite. By concentrating the filtrate, 12.5 g (98%) of the title compound was obtained.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. concentrationthe resulting filtrate was concentrated
  4. dissolutionThe resulting residue was dissolved in 300 ml of chloroform
  5. filtrationfiltered through celite
  6. concentrationBy concentrating the filtrate

Sources & evidence

ORD record
ord-cb898df2daa646feabb8b9f7f2dea8ba
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

Loading…