1,1-Dichloroethane → Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-formylaminophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1415948Notes

Reaction equation

HRID 1415948 reaction equation
ClC(Cl)C.[Cl:5][C:6]1[C:7]([F:34])=[C:8]([F:33])[CH:9]=[C:10]2[C:15]=1[N:14]([C:16]1[CH:21]=[C:20]([N+:22]([O-])=O)[C:19]([F:25])=[CH:18][C:17]=1[F:26])[CH:13]=[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:11]2=[O:32].[C:35](OC(=O)C)(=[O:37])C>[Pd].C(O)=O>[Cl:5][C:6]1[C:7]([F:34])=[C:8]([F:33])[CH:9]=[C:10]2[C:15]=1[N:14]([C:16]1[CH:21]=[C:20]([NH:22][CH:35]=[O:37])[C:19]([F:25])=[CH:18][C:17]=1[F:26])[CH:13]=[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:11]2=[O:32]

Participants

6

Reactant 3

HCID 63651,1-DichloroethaneHCID 7918Acetic AnhydrideHCID 54202503Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 54054955Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-formylaminophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

To 20 ml of dichloroethane and 10 ml of formic acid were added 2 g of ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate and 200 mg of 10% palladium on carbon. Under a hydrogen atmosphere, the solution was stirred at room temperature for 3 hours and after addition of acetic anhydride, further stirred overnight. The catalyst was removed by a membrane filter and the filtrate was concentrated in vacua. Diethyl ether was added to the residue whereupon the solid was collected by filtration and washed with ethanol and diethyl ether to give 1.9 g of the title compound.

Workup

  1. customThe catalyst was removed by a membrane
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated in vacua
  4. additionDiethyl ether was added to the residue whereupon the solid
  5. filtrationwas collected by filtration
  6. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-17d85fae8bb54008a85d3a7e1a9ebd41
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

Loading…