Acetic Acid → HCID 10971106, compound

HRID 1415931Notes

Reaction equation

HRID 1415931 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:22])=[C:18]([Cl:21])[N:19]=3)[C:14](=[O:23])[C:13]([C:24]([O:26]CC)=[O:25])=[CH:12]2)[C:5]([F:10])=[C:6]([F:9])[C:7]=1[F:8].C(O)(=O)C.ClC(Cl)C>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:22])=[C:18]([Cl:21])[N:19]=3)[C:14](=[O:23])[C:13]([C:24]([OH:26])=[O:25])=[CH:12]2)[C:5]([F:10])=[C:6]([F:9])[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 54318442HCID 54318442, compound

Product 1

HCID 10971106HCID 10971106, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 1-(3-amino-4,5,6-trifluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (600 mg) was dissolved in 30 ml of methanol, 10 ml of acetic acid, and 30 ml of dichloroethane, to which was added 100 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. To the residue were added 4 ml of acetic acid and 1 ml of hydrochloric acid. The solution was heated at 100° C. and stirred overnight. The reaction solution was concentrated in vacua whereupon diethyl ether was added to the residue. The solid was collected by filtration and washed with diethyl ether to give 160 mg of the title compound.

Workup

  1. customThe catalyst was removed by a membrane
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated in vacua
  4. additionTo the residue were added 4 ml of acetic acid and 1 ml of hydrochloric acid
  5. temperatureThe solution was heated at 100° C.
  6. stirringstirred overnight
  7. concentrationThe reaction solution was concentrated in vacua whereupon diethyl ether
  8. additionwas added to the residue
  9. filtrationThe solid was collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-60f78f64dcce40a28419c10d4427c6f7
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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