Acetic Acid → HCID 10586568, compound

HRID 1451086Notes

Reaction equation

HRID 1451086 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(O)(=O)C.[CH2:20](I)[CH:21]=[CH2:22]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:12]([O:11][C:9](=[O:10])[C:8]1[CH:14]=[CH:15][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([CH2:22][CH:21]=[CH2:20])[CH:7]=1)[CH3:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11166Allyl iodideHCID 220420Ethyl-4-acetamidobenzoate

Product 1

HCID 10586568HCID 10586568, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl-4-acetylaminobenzoate (Coneglio, L. Rend Acad. Sci. Napoli [3] 1931, 36, 56-60) (2.07 g, 0.01 mol) and palladium acetate (1.12 g, 0.005 mol) in dry toluene (17 mL) was heated at reflux for 0.75 h under nitrogen. The solution was cooled to 60° C., the toluene was decanted, and the residue was washed with fresh toluene. The combined filtrates were heated at reflux for 3 h, the precipitate was collected by filtration, and mixed with the previous residue. The combined greenish residues were dried under vacuum for 3 h. To this residue, glacial acetic acid (40 mL) and allyl iodide (8.40 g, 0.05 mol) were added and the mixture was stirred at room temperature for 16 h. The palladium was removed by filtration through Celite and the filtrate was concentrated. The residue was passed through a column of silica gel using 1:1 ethyl acetate:hexane as eluent to give 0.85 g (69%) of ethyl-4-acetylamino-3-allylbenzoate as a white powder, mp 127°-128° C.

Workup

  1. temperatureat reflux for 0.75 h under nitrogen
  2. customthe toluene was decanted
  3. washthe residue was washed with fresh toluene
  4. temperatureThe combined filtrates were heated
  5. temperatureat reflux for 3 h
  6. filtrationthe precipitate was collected by filtration
  7. additionmixed with the previous residue
  8. customThe combined greenish residues were dried under vacuum for 3 h
  9. customThe palladium was removed by filtration through Celite
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-19ea8c4b355d4e05851ad93642b79ab2
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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