HCID 22121269, compound → 5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610284Notes

Reaction equation

HRID 610284 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

Participants

4

Reactant 1

HCID 22121269HCID 22121269, compound

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-difluoropyridin-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-6ed0ee0b2e6648e79ab7591ef19286ef
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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