Ammonium formate → N-(4-Isopropyl-3-methoxy-phenyl)-acetamide

HRID 81854Notes

Reaction equation

HRID 81854 reaction equation
O[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[O:15][CH3:16])([CH3:4])[CH3:3].C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[O:15][CH3:16])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formate3×HCID 59598542HCID 59598542, compound

Product 1

HCID 59598686N-(4-Isopropyl-3-methoxy-phenyl)-acetamideYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide (16.4 g) in 100 ml glacial acetic acid was stirred at room temperature under N2, and palladium on activated carbon (3 g 10 Wt %) was added, followed by 5 g of ammonium formate. The reaction mixture was heated to reflux. After 30 minutes 5 g ammonium formate was added, and after 45 minutes another 8.5 g ammonium formate was added. Reflux was continued for another hour, then the reaction mixture was cooled, and filtered through Celite. The filtrate was diluted with water, extracted with EtOAc, and the combined organic layers were washed with brine and dried over magnesium sulfate. Evaporation under reduced pressure gave N-(4-Isopropyl-3-methoxy-phenyl)-acetamide (15.1 g, 99%).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperatureReflux
  3. waitwas continued for another hour
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered through Celite
  6. additionThe filtrate was diluted with water
  7. extractionextracted with EtOAc
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-45d0aa910bac49019eaca97b8764bc26
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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