Hydrochloric Acid → HCID 67916341, compound

HRID 1651595Notes

Reaction equation

HRID 1651595 reaction equation
[N:1](=[C:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:24])[C:13]([C:21]([OH:23])=[O:22])=[CH:14][N:15]3[CH:18]3[CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:25])[CH2:4]1)O.[H][H].[ClH:28]>[Ni].CN(C)C=O>[ClH:28].[NH2:1][CH:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:24])[C:13]([C:21]([OH:23])=[O:22])=[CH:14][N:15]3[CH:18]3[CH2:19][CH2:20]3)=[CH:10][C:9]=2[F:25])[CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86743975HCID 86743975, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67916341HCID 67916341, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 17.2 g (50 mmol) of 7-[(3-oximino)cyclopentyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 3.0 g of Raney-nickel and 300 ml of N,N-dimethylformamide was shaken in a hydrogen atmosphere at 45-50 psi for 24 hours. After removing the catalyst by filtration through Celite and addition of 100 ml of 6.0 M hydrochloric acid (60 mmol), the mixture was evaporated in high vacuo at 50° . The residue was triturated with a mixture of 200 ml of ethanol/ether (1:1) and the solid was removed by filtration, washed with ethanol/ether (1:1) and dried in vacuo to give 13.1 g of the title compound.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customthe mixture was evaporated in high vacuo at 50°
  4. customThe residue was triturated with a mixture of 200 ml of ethanol/ether (1:1)
  5. customthe solid was removed by filtration
  6. washwashed with ethanol/ether (1:1)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8ad784261a9c4526967f0a34fe25e3ec
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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