HCID 54231342, compound → HCID 23284779, compound

HRID 1415964Notes

Reaction equation

HRID 1415964 reaction equation
[Cl:1][C:2]1[C:3]([F:30])=[C:4]([F:29])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[CH:14][C:13]=1[Cl:22])[CH:9]=[C:8]([C:23]([O:25]CC)=[O:24])[C:7]2=[O:28]>[Fe].C(O)=O>[NH2:18][C:16]1[CH:17]=[C:12]([N:10]2[C:11]3[C:6](=[CH:5][C:4]([F:29])=[C:3]([F:30])[C:2]=3[Cl:1])[C:7](=[O:28])[C:8]([C:23]([OH:25])=[O:24])=[CH:9]2)[C:13]([Cl:22])=[CH:14][C:15]=1[F:21]

Participants

4

Reactant 1

HCID 54231342HCID 54231342, compound

Product 1

HCID 23284779HCID 23284779, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 5 ml of formic acid were added 1.5 g of ethyl 8-chloro-6,7-difluoro-1-(2-chloro-4-fluoro-5-nitrophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate and 2 g of iron. The solution was heated and stirred at 60° C. for 2 hours. The insoluble was removed by filtration through celite and washed with formic acid and chloroform. The filtrate was concentrated in vacua. Ethanol was added to the residue whereupon the solid was collected by filtration and washed with diethyl ether. To the solid were added 4 ml of conc. hydrochloric acid and 4 ml of acetic acid. The solution was heated at reflux for 1 hour and allowed to cool down. The precipitated was collected by filtration and washed with ethanol and diethyl ether to give 970 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. customThe insoluble was removed by filtration through celite
  3. washwashed with formic acid and chloroform
  4. concentrationThe filtrate was concentrated in vacua
  5. additionEthanol was added to the residue whereupon the solid
  6. filtrationwas collected by filtration
  7. washwashed with diethyl ether
  8. additionTo the solid were added 4 ml of conc. hydrochloric acid and 4 ml of acetic acid
  9. temperatureThe solution was heated
  10. temperatureat reflux for 1 hour
  11. temperatureto cool down
  12. filtrationThe precipitated was collected by filtration
  13. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-c6aa12c8fb274ff994c9aa6a61994def
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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