Water → 6-Methoxy-2-pyridinecarbonitrile

HRID 1437208Notes

Reaction equation

HRID 1437208 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[N:6]=1.O.C(OCC)(=O)C>CN(C)C=O>[CH3:12][O:11][C:7]1[N:6]=[C:5]([C:2]#[N:3])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2568102-Bromo-6-methoxypyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 130236446-Methoxy-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
165 °C

Procedure

Copper(I) cyanide (2.68 g) was added to 2-bromo-6-methoxypyridine (5.62 g) in N,N-dimethylformamide (112 mL) at room temperature, followed by stirring at 165° C. for 15 hours. The resultant mixture was cooled in air. Water and ethyl acetate was added to the mixture. The insoluble matter that was formed in the mixture was filtered by Celite. The filtrate was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid substance (1.78 g, 44%).

Workup

  1. customThe insoluble matter that was formed in the mixture
  2. filtrationwas filtered by Celite
  3. customThe filtrate was partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1693acca8ef3476680cd75e42a9e8446
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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