Sodium Cyanide → 3-Methoxypyridine-2-carbonitrile

HRID 983412Notes

Reaction equation

HRID 983412 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C-:10]#[N:11].[Na+]>CS(C)=O>[CH3:9][O:8][C:7]1[C:2]([C:10]#[N:11])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 113324933-Methoxypyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-3-methoxy-pyridine from Example 13a in DMSO is treated with NaCN at 120° C. for 18 h. The reaction mixture is evaporated, the residue is taken into ethyl acetate, washed with 5% Na2CO3 (aqueous), dried over MgSO4 and evaporated to give 3-methoxy-pyridine-2-carbonitrile.

Workup

  1. customThe reaction mixture is evaporated
  2. washwashed with 5% Na2CO3 (aqueous)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-502faba2f974483ca1961d2bb4780eec
Source dataset
uspto-grants-2005_03
Patent number
US06864267B2

Reaction notes

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