Potassium Hydroxide → 2-Amino-4-methylbenzamide

HRID 1750871Notes

Reaction equation

HRID 1750871 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH-:11].[K+]>C(O)C>[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]([NH2:5])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 28014742-Amino-4-methylbenzamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-4-methylbenzonitrile (10 g, 75.7 mmol) was dissolved in ethanol, added with potassium hydroxide (21.2 g, 378 mmol), followed by refluxing for 8 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in ethyl acetate. The organic layer formed was washed with a saturated aqueous solution of sodium bicarbonate and brine. The obtained organic layer is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethanol to obtain the title compound (4.9 g, 43%).

Workup

  1. temperatureby refluxing for 8 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. customThe organic layer formed
  5. washwas washed with a saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialThe obtained organic layer is dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0d8b44d183164488a6f30a2825f2195f
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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