Water → 5-Methylpicolinonitrile

HRID 927408Notes

Reaction equation

HRID 927408 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C-:9]#[N:10].[Na+].O>CS(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 741835-MethylpicolinonitrileYield 30.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-fluoro-5-methylpyridine (CAN: 2369-19-9, 10 g, 90 mmol) and sodium cyanide (8.8 g, 180 mmol) in DMSO (15 mL) was heated to 150° C. for 48 h. Then water was added, the resulting mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were washed with sodium hypochlorite solution and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 40 g, 10% ethyl acetate in petroleum ether) to yield the title compound (3.2 g, 27 mmol, 30.1%) as yellow solid; MS (EI): m/e=119.1 [M+H]+.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
  2. washthe combined extracts were washed with sodium hypochlorite solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel, 40 g, 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cb9bbf4dea3b487cb14b200410205d34
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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