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

HRID 600868Notes

Reaction equation

HRID 600868 reaction equation
F[C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[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].O.[NH3:28]>CN(C)C=O.CO>[NH2:28][C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[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]

Participants

5

Reactant 2

HCID 11014105Ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylateHCID 12896473Azane;hydrate

Product 1

HCID 67271091ethyl 6-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 6,7-difluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate (10.04 g, 27.12 mmol) was dissolved in dimethylformamide (150 ml), and 28% ammonia water (32.1 ml) was added dropwise thereto while stirring and cooling with ice. While sealing the reaction solution in a sealed tube, it was stirred at room temperature for 4 hours. The reaction solution was then dissolved in methanol (200 ml) and concentrated under a reduced pressure. The residue obtained was purified by recrystallization from a mixed solvent of 2-propanol/chloroform/28% ammonia water, and after drying under a reduced pressure, 7.07 g (71%) of the title compound was obtained as a yellow powder.

Workup

  1. temperaturecooling with ice
  2. stirringit was stirred at room temperature for 4 hours
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue obtained
  5. customwas purified by recrystallization from a mixed solvent of 2-propanol/chloroform/28% ammonia water
  6. customafter drying under a reduced pressure

Sources & evidence

ORD record
ord-2ddb0a11161d49ac8aa9f9d663b51bfc
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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