Potassium Carbonate → 1-(4-Amino-2,6-dimethoxyphenyl)ethan-1-one

HRID 491504Notes

Reaction equation

HRID 491504 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([NH:12]C(=O)C(F)(F)F)=[CH:6][C:5]=1[O:19][CH3:20])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:12][C:7]1[CH:6]=[C:5]([O:19][CH3:20])[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([O:10][CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11197062HCID 11197062, compound

Product 1

HCID 576784271-(4-Amino-2,6-dimethoxyphenyl)ethan-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(4-Acetyl-3,5-dimethoxy-phenyl)-2,2,2-trifluoro-acetamide (4.3 g, 14.8 mmol) dissolved in methanol (90 mL) was added anhydrous potassium carbonate (4.67 g, 33.8 mmol). After refluxing for 18 hours, the reaction mixture was cooled and concentrated under reduced pressure. The concentrate was extracted with ethyl acetate and the organic layer was washed with brine, dried using anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1-(4-Amino-2,6-dimethoxy-phenyl)-ethanone (2.5 g, 87%) as a pale yellow solid.

Workup

  1. temperatureAfter refluxing for 18 hours
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. extractionThe concentrate was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f472b442f254b71b7c5054ce9b1694b
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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