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

HRID 1717281Notes

Reaction equation

HRID 1717281 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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH3:24]>CC(C)=O>[CH2:23]([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])[CH3:24]

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 (2.1 g) obtained in Example 74a) in acetone (100 ml) were added potassium carbonate (1.4 g) and bromoethane (0.75 ml), and the mixture was heated under reflux overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the organic layer was fractionated. The organic layer was dried over 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 mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-647b9f725cd9433cbdf87cf08bbe8569
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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