Potassium Carbonate → HCID 18974768, compound

HRID 726514Notes

Reaction equation

HRID 726514 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[N:11]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:10]2[N:11]=[C:12]([C:16]#[N:17])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 21226206Ethyl acetate hexaneHCID 178516507HCID 178516507, compound

Product 1

HCID 18974768HCID 18974768, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-hydroxypyridine (38.9 g, 0.3 mol), 2-chloro-6-cyanopyridine (45.7 g, 0.3 mol), and potassium carbonate (45.6 g, 0.3 mol) in N,N-dimethylformamide is refluxed for three hours, cooled and diluted with water and ethyl acetate. The resultant mixture is filtered through a layer of silica gel using ethyl acetate as eluent. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic extract is combined with the organic phase and the resultant solution is washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 7:3 hexane/ethyl acetate solution gives the title product as light brown crystals (56.5 g, 81.3%, mp 114° C.).

Workup

  1. temperatureis refluxed for three hours
  2. temperaturecooled
  3. filtrationThe resultant mixture is filtered through a layer of silica gel
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. extractionThe organic extract
  7. washthe resultant solution is washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto obtain a residue

Sources & evidence

ORD record
ord-7c7db4b1228544db857285ea4fd3c1a0
Source dataset
uspto-grants-1998_01
Patent number
US05710106

Reaction notes

Loading…