Acetic Acid → HCID 54253406, compound

HRID 1415929Notes

Reaction equation

HRID 1415929 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:24])=[C:19]([F:23])[C:20]=2[F:22])[C:15](=[O:25])[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:13]1.C(O)(=O)C.ClC(Cl)C>CO.[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:24])=[C:19]([F:23])[C:20]=3[F:22])[C:15](=[O:25])[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:13]2)[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 53748582HCID 53748582, compound

Product 1

HCID 54253406HCID 54253406, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 1-(2,4-difluoro-5-nitrophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (2.2 g) was dissolved in 20 ml of methanol, 50 ml of acetic acid, and 10 ml of dichloroethane, to which was added 200 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 1.12 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-ed27717053ff48d1ba3c89c633194d5f
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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