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

HRID 862441Notes

Reaction equation

HRID 862441 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

To a cooled (0° C.) solution of sodium cyanide (49.0 g, 0.999 mol, 3.0 eq.) in 135 mL of water (air free) was dripped 1-methoxy-3,5-dimethyl pyridinium methyl sulfate (83.0g, 0.33 mol) in 100 mL water (air free) in 1.25 hr., keeping the temperature below 3° C. The reaction mixture was stored at about 3° C. overnight. The mixture was filtered and washed with water to give 40 g of the title compound. An analytical sample was recrystallized from isopropyl ether and pentane (4:1) (m.p.: 61°-62° C.).

Workup

  1. customin 1.25 hr
  2. customthe temperature below 3° C
  3. filtrationThe mixture was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-ba997c8799ad4f7b8fb5821abbe09698
Source dataset
uspto-grants-1998_02
Patent number
US05719148

Reaction notes

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