Acetic Acid → HCID 11013582, compound

HRID 1415956Notes

Reaction equation

HRID 1415956 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:26])[C:7]([C:22]([O:24]C)=[O:23])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([N+:19]([O-])=O)[CH:13]=2)=[CH:4][C:3]=1[F:27].C(O)(=O)C.ClC(Cl)C>CO.[Pd]>[NH2:19][C:14]1[CH:13]=[C:12]([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:27])=[C:2]([Cl:1])[N:11]=3)[C:6](=[O:26])[C:7]([C:22]([OH:24])=[O:23])=[CH:8]2)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 54419689HCID 54419689, compound

Product 1

HCID 11013582HCID 11013582, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 7-chloro-6-fluoro-1-(4-fluoro-3-nitrophenyl)-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, and 100 mg of 10% palladium on carbon was added thereto. Under a hydrogen atmosphere, the solution was stirred at room temperature overnight. 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 and stirred at 100° C. overnight. The reaction solution was concentrated in vacua. Diethyl ether was added to the residue whereupon 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
  6. stirringstirred at 100° C. overnight
  7. concentrationThe reaction solution was concentrated in vacua
  8. additionDiethyl ether was added to the residue whereupon the solid
  9. filtrationwas collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-cdbd7bf9f65745ecb2acf5101c6b4c2c
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

Loading…