Sodium Cyanide → 3,5-dimethylpyridine-2-carbonitrile

HRID 1030095Notes

Reaction equation

HRID 1030095 reaction equation
[C-:1]#[N:2].[Na+].COS([O-])(=O)=O.CO[N+:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1>O>[C:1]([C:13]1[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[CH:17][N:12]=1)#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18382727HCID 18382727, compound

Product 1

HCID 81672693,5-dimethylpyridine-2-carbonitrileYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Cool a solution of sodium cyanide (49.0 g, 0.999 mol, 3.0 eq.) in 135 mL of water to 0° C., (air free) and drip 1-methoxy-3,5-dimethyl pyridinium methyl sulfate (83.0 g, 0.33 mol) in 100 mL water (air free) over 11/4 hr., keeping the temperature below 3° C. Filter the mixture and wash with water to give 40 g of the title compound which may be recrystallized from isopropyl ether and pentane (4:1) (m.p. 61°-62° C.).

Workup

  1. custom4 hr
  2. customthe temperature below 3° C
  3. filtrationFilter the mixture
  4. washwash with water

Sources & evidence

ORD record
ord-bdf7a13d2a904d42b87ab99627907dc6
Source dataset
uspto-grants-1992_04
Patent number
US05104876

Reaction notes

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