Ethyl Bromide → 3-ethoxy-N-ethyl-4-nitrobenzamide

HRID 1717328Notes

Reaction equation

HRID 1717328 reaction equation
[CH2:1]([NH:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([OH:14])[CH:6]=1)[CH3:2].[CH2:16](Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:14][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12])[C:4]([NH:3][CH2:1][CH3:2])=[O:15])[CH3:17]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 21029708N-ethyl-3-hydroxy-4-nitrobenzamide

Product 1

HCID 685151263-ethoxy-N-ethyl-4-nitrobenzamideYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-ethyl-3-hydroxy-4-nitrobenzamide (2.10 g) obtained in Example 131a) in acetone (100 ml) were added ethyl bromide (0.75 ml) and potassium carbonate (1.38 g), and the reaction mixture was heated under reflux overnight. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. Ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a pale-brown solid (0.72 g, 30%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solvent was evaporated under reduced pressure
  4. additionEthyl acetate and water were added to the residue
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ead7259b1fd45b5bfccfd41b0cf1cd1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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