18-Crown-6 → HCID 45082638, compound

HRID 357525Notes

Reaction equation

HRID 357525 reaction equation
Cl[C:2]1[N:7]=[C:6]2[C:8]([O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1)=[O:9].[F-:13].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)CC>[F:13][C:2]1[N:7]=[C:6]2[C:8]([O:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1)=[O:9]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 154810682-chloro-5H,7H-furo(3,4-b)pyridine-5,7-dione

Product 1

HCID 45082638HCID 45082638, compound

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A mixture of 36.7 g (0.2 mol) of 6-chloropyridine-2,3-dicarboxylic anhydride, 17.4 g (0.3 mol) of potassium fluoride and 1 g of 18-crown-6 in 200 ml of propionitrile were stirred for 10 hours while refluxing. After cooling, the reaction mixture was filtered with suction and the residue was washed with methylene chloride. The filtrate was evaporated down under reduced pressure and stirred with a 2:1 methyl tert-butyl ether/pentane mixture, and the product was filtered off with suction and dried. 25.3 g (76% of theory) of the title compound of melting point 106° C. (decomposition) were obtained.

Workup

  1. temperaturewhile refluxing
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered with suction
  4. washthe residue was washed with methylene chloride
  5. customThe filtrate was evaporated down under reduced pressure
  6. stirringstirred with a 2:1 methyl tert-butyl ether/pentane mixture
  7. filtrationthe product was filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-360e3d97785b410b8071f2b78965e5df
Source dataset
uspto-grants-1998_11
Patent number
US05840904

Reaction notes

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