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Ethyl 1-(6-t-butylamino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate → 5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368507
Notes
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Reaction equation

HRID 368507 reaction equation
C([NH:5][C:6]1[N:11]=[C:10]([N:12]2[C:21]3[C:16](=[C:17]([N+:25]([O-])=O)[C:18]([F:24])=[C:19]([F:23])[C:20]=3[Cl:22])[C:15](=[O:28])[C:14]([C:29]([O:31]CC)=[O:30])=[CH:13]2)[C:9]([F:34])=[CH:8][C:7]=1[F:35])(C)(C)C>[Fe].C(O)=O>[NH2:25][C:17]1[C:18]([F:24])=[C:19]([F:23])[C:20]([Cl:22])=[C:21]2[C:16]=1[C:15](=[O:28])[C:14]([C:29]([OH:31])=[O:30])=[CH:13][N:12]2[C:10]1[C:9]([F:34])=[CH:8][C:7]([F:35])=[C:6]([NH2:5])[N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 22121269Ethyl 1-(6-t-butylamino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221211655-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 83.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To 10 ml of formic acid was added 960 mg of ethyl 1-(6-t-butylamino-3,5-difluoropyridine-2-yl)-8-chloro-6,7-difluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate together with 1.0 g of iron powder, and the mixture was stirred at 80 to 90° C. for 5 hours and 40 minutes. The insoluble content was separated by filtration through celite, and the content separated by the celite and the celite were washed with formic acid and chloroform. The filtrate and the washings were concentrated under reduced pressure. To the residue was added the 6 ml of the mixed solution of 4N hydrochloric acid and acetic acid (1:1), and the mixture was heated under reflux for 2 hours with stirring and allowed to cool. The precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 625 mg of the title compound as a yellow powder.

Workup

  1. customThe insoluble content was separated by filtration through celite
  2. customthe content separated by the celite
  3. washthe celite were washed with formic acid and chloroform
  4. concentrationThe filtrate and the washings were concentrated under reduced pressure
  5. additionTo the residue was added the 6 ml of the mixed solution of 4N hydrochloric acid and acetic acid (1:1)
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 2 hours
  8. stirringwith stirring
  9. temperatureto cool
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-58445e950ec544d5a3eb0e9c2dd5e867
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133284

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes