Sodium Thiosulfate → 7-Fluoro-1,5-naphthyridine 1-oxide

HRID 385614Notes

Reaction equation

HRID 385614 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.ClC1C=CC=C(C(OO)=[O:20])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-:20])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 534161913-Fluoro-1,5-naphthyridine

Product 1

HCID 578152157-Fluoro-1,5-naphthyridine 1-oxideYield 71.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 76 mg of 3-fluoro-1,5-naphthyridine in 3 mL of chloroform, 136 mg of m-chloroperbenzoic acid was added, and the mixture was stirred at room temperature for 2.5 hours. Thereto was added 27 mg of m-chloroperbenzoic acid, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, a 5% aqueous sodium thiosulfate solution and chloroform were added, the organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60N made by KANTO CHEMICAL CO., INC., and an eluent of chloroform:methanol=50:1 to obtain 60 mg of 7-fluoro-1,5-naphthyridine 1-oxide as a light yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a2a52cae5c8d4cb6a798a8fe69ffd52c
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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