p-Aminoacetophenone → HCID 2994007, compound

HRID 2405026Notes

Reaction equation

HRID 2405026 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].C([O-])(O)=O.[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O.O1CCOCC1>[CH2:20]([O:19][C:17](=[O:18])[NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7468p-AminoacetophenoneHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 2994007HCID 2994007, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 10 g of 4-aminoacetophenone (74 mmol, 1 eq) in a mixture of 60 ml of water and 100 ml of dioxane at 0° C., 12.43 g of NaHCO3 (148 mmol, 2 eq) and 15.3 g of benzyl chloroformate (85 mmol, 1.15 eq, purity 95%) are added. The mixture is stirred at room temperature for 4 h and then concentrated under reduced pressure to remove the dioxane. The suspension is diluted with 70 ml of water and 150 ml of ethyl acetate. The phases are separated and the organic layer is washed with 2×50 ml of brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 19.5 g of the product as solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the dioxane
  3. additionThe suspension is diluted with 70 ml of water and 150 ml of ethyl acetate
  4. customThe phases are separated
  5. washthe organic layer is washed with 2×50 ml of brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05b81ddee8b547ff81a56de1f1d60c4a
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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