HCID 14770861, compound → HCID 67916341, compound

HRID 1090398Notes

Reaction equation

HRID 1090398 reaction equation
C([NH:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[C:15]([C:23]([O:25]CC)=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:29])[CH2:6]1)(=O)C.[ClH:30].C(O)C>>[ClH:30].[NH2:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[C:15]([C:23]([OH:25])=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:21][CH2:22]3)=[CH:12][C:11]=2[F:29])[CH2:6]1

Participants

3

Reactant 2

HCID 14770861HCID 14770861, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 67916341HCID 67916341, compound

Procedure

A mixture of 20.0 g (50 mmol) of 7-[3-(acetylamino)cyclopentyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, ethyl ester was heated in a mixture of 6.0 M hydrochloric acid/ethanol (20 ml/150 ml) at reflux for 8 hours. The solvent was removed in vacuo and the residue slurried in 200 ml of water and filtered. The filtrate was evaporated in vacuo and the residue triturated in ethanol and filtered. The precipitate was washed with ethanol, ether, and dried in vacuo to give 13.6 g of the title compound.

Workup

  1. temperatureat reflux for 8 hours
  2. customThe solvent was removed in vacuo
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue triturated in ethanol
  6. filtrationfiltered
  7. washThe precipitate was washed with ethanol, ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-096dbf635a1d42598b648c1b892d22dc
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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