Hexane → Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxyl ate

HRID 600870Notes

Reaction equation

HRID 600870 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[C:4]([N+:23]([O-])=O)[CH:3]=1.CCCCCC>C(#N)C.[C].[Pd].C(OCC)(=O)C>[NH2:23][C:4]1[CH:3]=[C:2]([F:1])[C:11]([CH3:12])=[C:10]2[C:5]=1[C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[C@@H:13]1[CH2:15][C@@H:14]1[F:16]

Participants

6

Reactant 2

HCID 8058HexaneHCID 67272057Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate

Product 1

HCID 67270424Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxyl ateYield 38%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate (2.50 g, 7.10 mmol) was dissolved in acetonitrile (20 ml), and after adding a 5% palladium carbon catalyst (water content: 50%, 1.0 g) thereto, it was stirred at room temperature for 20 hours under a hydrogen atmosphere at atmospheric pressure. After removing the catalyst by filtering (methanol washing), the filtrate was concentrated under a reduced pressure, and the residue obtained was dissolved in ethyl acetate (10 ml) and heated under reflux for 30 minutes. n-hexane (10 ml) was then added, and after performing heated refluxing for 30 minutes, there action solution was allowed to stand under room temperature. The precipitated crystals were then filtered out, washed with a 1:1 mixed solution of n-hexane:ethyl acetate and dried under a reduced pressure at 60° C. for 16 hours. 869 mg (38%) of the title compound was thereby obtained as a yellow powder.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtering (methanol washing)
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customthe residue obtained
  5. temperatureheated
  6. temperatureunder reflux for 30 minutes
  7. temperatureafter performing heated
  8. temperaturerefluxing for 30 minutes
  9. customto stand under room temperature
  10. filtrationThe precipitated crystals were then filtered out
  11. washwashed with a 1:1 mixed solution of n-hexane
  12. dry with materialethyl acetate and dried under a reduced pressure at 60° C. for 16 hours

Sources & evidence

ORD record
ord-ff1e5ba4a316439297feea033e51fd13
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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