Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate → Ethyl 1-(3-amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1415927Notes

Reaction equation

HRID 1415927 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]1[C:21]2[C:16](=[CH:17][C:18]([F:23])=[C:19]([F:22])[CH:20]=2)[C:15](=[O:24])[C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13]1>C(O)(=O)C.[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:23])=[C:19]([F:22])[CH:20]=3)[C:15](=[O:24])[C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13]2)[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

4

Reactant 1

HCID 15860364Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 54141710Ethyl 1-(3-amino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (3.7 grams) was dissolved in 60 ml of acetic acid, to which was added 400 mg of 10% palladium on carbon. Under a hydrogen atmosphere, the solution was stirred for 2 days at room temperature. The catalyst was removed by a membrane filter and 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 give 2.9 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-18279553907b45efa0cb5b58eaee76c3
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

Loading…