Acetic Acid → HCID 54383776, compound

HRID 1415932Notes

Reaction equation

HRID 1415932 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([C:13]1[CH:18]=[C:17]([N+:19]([O-])=O)[C:16]([F:22])=[C:15]([F:23])[C:14]=1[F:24])[CH:7]=[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2=[O:30].C(O)(=O)C.ClC(Cl)C>C(O)C.[Pd]>[NH2:19][C:17]1[CH:18]=[C:13]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([F:1])=[C:11]([F:12])[CH:10]=3)[C:5](=[O:30])[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:7]2)[C:14]([F:24])=[C:15]([F:23])[C:16]=1[F:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 54309158HCID 54309158, compound

Product 1

HCID 54383776HCID 54383776, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 6,7-difluoro-1,4-dihydro-4-oxo-1-(2,3,4-trifluoro-5-nitrophenyl)quinoline-3-carboxylate (280 mg) was dissolved in 10 ml of ethanol, 5 ml of acetic acid, and 5 ml of dichloroethane, to which was added 30 mg of 10% palladium on carbon. Under a hydrogen atmosphere, the solution was stirred overnight 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 200 mg 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-c8cb344d6b72414e801f87c828c8d0ca
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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