Water → N-[3-Bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethyl-N-2-propen-1-ylpropanamide

HRID 1943132Notes

Reaction equation

HRID 1943132 reaction equation
[Br:1][C:2]1[C:3]([N:9]([CH2:16][CH:17]=[CH2:18])[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:19][O-:20].[Na+].O>CO>[Br:1][C:2]1[C:3]([N:9]([CH2:16][CH:17]=[CH2:18])[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:4][C:5]([O:20][CH3:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86642089N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethyl-N-2-propen-1-ylpropanamide

Product 1

HCID 68598002N-[3-Bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethyl-N-2-propen-1-ylpropanamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethyl-N-2-propen-1-ylpropanamide (12.388 g, 37.370 mmol) in methanol (100 ml) at rt under argon was treated with sodium methoxide solution (25% w/v in methanol, 17.76 g, 82.212 mmol) and then heated at reflux for 42 h. The reaction was then cooled, treated with water (500 ml), and extracted with diethyl ether (3×200 ml). The organic extracts were dried (MgSO4), and evaporated to give the product (10.918 g, 89%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 42 h
  3. temperatureThe reaction was then cooled
  4. extractionextracted with diethyl ether (3×200 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-942787a477994598b3bbe957fe476f36
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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