Sodium Cyanide → 5-Methylpicolinonitrile

HRID 927431Notes

Reaction equation

HRID 927431 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 CyanideHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 741835-MethylpicolinonitrileYield 249.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

2-Fluoro-5-methylpyridine (CAN 2369-19-9, 50 g, 90 mmol) and sodium cyanide (CAN 143-33-9, 70 g, 1.43 mol) were dissolved in DMSO (200 mL), the mixture was stirred for 3 days at 150° C. The mixture was cooled to room temperature, ice water (200 mL) was added and the product was obtained as red solid (26.5 g, 50%) by filtration and drying; MS (EI): m/e 119.1 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-f61e3e874cfc424591b0493a9ab774f0
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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