Sodium Cyanide → 5-Methylpicolinonitrile

HRID 1166366Notes

Reaction equation

HRID 1166366 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C-:9]#[N:10].[Na+]>CS(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 741835-MethylpicolinonitrileYield 40.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-fluoro-5-methylpyridine (39 g; 351.5 mmol) in 141 ml of dimethylsulfoxide was added 17.23 g of sodium cyanide (351.5 mmol). After stirring for 3 days at 150° C., an additional 3 g of sodium cyanide was added and heating was continued for 5 hours. The reaction mixture was cooled to 25° C. then poured into 525 ml of ice water. The solution was filtered through a coarse fritted funnel and a dark brown solid was collected. The solid was air dried to give 17 g of the desired cyanopyridine: Anal Calc'd. for C7H6N2: C, 71.17; H, 5.12; N, 23.71. Found: C, 69.91; H, 5.24; N, 23.26.

Workup

  1. temperatureheating
  2. waitwas continued for 5 hours
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. filtrationThe solution was filtered through a coarse fritted funnel
  5. customa dark brown solid was collected
  6. customdried

Sources & evidence

ORD record
ord-9a77cc8485004236868433feffe85896
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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