HCID 53738908, compound → HCID 54318442, compound

HRID 1415930Notes

Reaction equation

HRID 1415930 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:29])[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:8][N:9]2[C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[C:14]([F:22])[C:13]=2[F:23])=[CH:4][C:3]=1[F:30]>CO.C(O)(=O)C.[Pd]>[NH2:18][C:16]1[CH:17]=[C:12]([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:30])=[C:2]([Cl:1])[N:11]=3)[C:6](=[O:29])[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:8]2)[C:13]([F:23])=[C:14]([F:22])[C:15]=1[F:21]

Participants

5

Reactant 1

HCID 53738908HCID 53738908, compound

Product 1

HCID 54318442HCID 54318442, compoundYield 27.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(2,3,4-trifluoro-5-nitrophenyl)-1,8-naphthyridine-3-carboxylate (780 mg) was dissolved in 5 ml of methanol and 10 ml of acetic acid, to which was added 80 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-f4eb30651a7c47998106c4be09aaff00
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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