N-bromobutanimide → 6-Bromo-3-methoxypicolinonitrile

HRID 983413Notes

Reaction equation

HRID 983413 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:9]#[N:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][C:6]1[N:5]=[C:4]([C:9]#[N:10])[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 113324933-Methoxypyridine-2-carbonitrile

Product 1

HCID 225607406-Bromo-3-methoxypicolinonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-methoxy-pyridine-2-carbonitrile from Example 13b in CCl4 is treated with N-bromosuccinimide (1 equiv.) and catalytic 2,2-azobisisobutyronitrile and is heated at reflux for 18 h. The reaction mixture is evaporated, the residue is taken into ethyl acetate, washed with 5% Na2CO3 (aqueous), 5 % Na2S2O3 (aqueous), dried over MgSO4 and evaporated to give 6-bromo-3-methoxy-pyridine-2-carbonitrile.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 h
  3. customThe reaction mixture is evaporated
  4. washwashed with 5% Na2CO3 (aqueous), 5 % Na2S2O3 (aqueous)
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-bcbb2527f67f4b7eaece1a3c9a9dd2c5
Source dataset
uspto-grants-2005_03
Patent number
US06864267B2

Reaction notes

Loading…