Potassium Hydroxide → HCID 22933386, compound

HRID 1269845Notes

Reaction equation

HRID 1269845 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C(C)(C)C)=[C:5]([CH3:16])[C:4]=1[C:17]([F:20])([F:19])[F:18].[OH-].[K+].[OH-].[Na+]>C(O)CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH3:16])[C:4]=1[C:17]([F:18])([F:20])[F:19]

Participants

5

Procedure

N-[4-methoxy-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide (3.15 g, 10.9 mmol) and potassium hydroxide (3.20 g, 57.1 mmol) were slowly heated to 160° C. in ethylene glycol (31.0 ml) and stirred for 20 hours while maintaining the temperature. The reaction solution was portioned and extracted with water and chloroform, and the organic phase was extracted with a 1N aqueous hydrochloric acid solution to obtain an aqueous phase. This aqueous phase was made basic with a 2N aqueous sodium hydroxide solution and extracted three times with chloroform. The combined organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain 4-methoxy-2-methyl-3-(trifluoromethyl)-aniline (1.10 g, 49%).

Workup

  1. temperaturewhile maintaining the temperature
  2. extractionextracted with water and chloroform
  3. extractionthe organic phase was extracted with a 1N aqueous hydrochloric acid solution
  4. customto obtain an aqueous phase
  5. extractionextracted three times with chloroform
  6. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb7cab936f27442e868a13efb863727f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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