Water → 2-(1',3'-Dimethyl-pyrazol-5-yloxy)-pyridine-6-carbonitrile

HRID 725748Notes

Reaction equation

HRID 725748 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[CH:5][C:4]([CH3:8])=[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+].O>CN(C)C=O>[CH3:1][N:2]1[C:6]([O:7][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[N:11]=2)=[CH:5][C:4]([CH3:8])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 178429390HCID 178429390, compound

Product 1

HCID 813466732-(1',3'-Dimethyl-pyrazol-5-yloxy)-pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.6 g of 1,3-dimethyl-5-hydroxypyrazole (50 mmol) was added to a suspension of 7.7 g 2-chloro-6-cyanopyridine (55 mmol) and 7.6 g K2CO3 (55 mmol) in 50 ml N,N-dimethylformamide and heated to reflux with vigorous stirring for 5 hours. After cooling, the mixture was poured into water (100 ml) and the aqueous layer extracted 3 times with each 100 ml ethyl acetate. The combined extracts were dried with anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by flash silica gel column chromatography using hexane/ethyl acetate 7/3. The title compound was obtained after recrystallisation from isopropanol as 5.9 g (55%) of white crystals of m.p. 95° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. extractionthe aqueous layer extracted 3 times with each 100 ml ethyl acetate
  5. dry with materialThe combined extracts were dried with anhydrous magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-1da1c6faa08e47bdb9cc278c38e62901
Source dataset
uspto-grants-1998_01
Patent number
US05707933

Reaction notes

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