Methanol → HCID 22441007, compound

HRID 1415933Notes

Reaction equation

HRID 1415933 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([Cl:20])[N:18]=3)[C:13](=[O:22])[C:12]([C:23]([O:25]CC)=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[Cl:8].CO.ClC(Cl)C>C(O)(=O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([Cl:20])[N:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 63651,1-DichloroethaneHCID 54120064HCID 54120064, compound

Product 1

HCID 22441007HCID 22441007, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

Ethyl 1-(3-amino-4-chloro-6-fluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (1.00 g) was dissolved in 10 ml of acetic acid, 10 ml of methanol and 20 ml of dichloroethane, to which was added a suspension of 132 mg of 10% palladium on carbon in 20 ml of acetic acid. Under a hydrogen atmosphere, the solution was stirred overnight. The palladium on carbon was removed by a membrane filter and 10% sodium hydroxide was added to the filtrate, which was extracted with chloroform. The organic layer was dried, and the solvent was distilled off. The solid was collected by filtration, to give 0.380 g of the title compound.

Workup

  1. customThe palladium on carbon was removed by a membrane
  2. filtrationfilter
  3. addition10% sodium hydroxide was added to the filtrate, which
  4. extractionwas extracted with chloroform
  5. customThe organic layer was dried
  6. distillationthe solvent was distilled off
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-0cbd7a7cdf054c92b888cab9098095d4
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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