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Acetic Acid → 5-amino-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1458007
Notes
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Reaction equation

HRID 1458007 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].C(O)(=O)C.Cl>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11759598Ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

Product 1

HCID 110233625-amino-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A 10.43 g (30.6 mmol) portion of ethyl 5-amino-6,7-difluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate was mixed with 150 ml of acetic acid and 150 ml of concentrated hydrochloric acid and then heated under reflux for 1 hour. After completion of the reaction, the reaction solution was spontaneously cooled and mixed with 700 ml of water. The thus formed crystals were collected by filtration, washed with water (100 ml×2), ethanol (300 ml×1) and ether (300 ml×1) in that order and then dried to yield 7.52 g (79%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was spontaneously cooled
  5. filtrationThe thus formed crystals were collected by filtration
  6. washwashed with water (100 ml×2), ethanol (300 ml×1) and ether (300 ml×1) in that order
  7. customdried

Sources & evidence

ORD record
ord-2d795fe8efbf4ddb88450310da64d819
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05849757

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes