Pyridine → (3-Acetamidophenyl) acetate

HRID 1802067Notes

Reaction equation

HRID 1802067 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10](OC(C)=O)=[O:11].N1[CH:21]=[CH:20]C=CC=1.C([O-])(O)=[O:23].[Na+]>>[C:10]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:20](=[O:23])[CH3:21])[CH:3]=1)(=[O:11])[CH3:9]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 115683-AminophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 231988(3-Acetamidophenyl) acetateYield 93%

Conditions

Temperature
80 °C

Procedure

3-aminophenol (19 g, 17 mol) was dissolved in Ac2O (162 g, 1.59 mol, 9.5 eq.), and pyridine (4.9 g, 0.062 mol, 0.36 eq.) was added. Then the reaction mixture was stirred at 80° C. over 2 h. Ice water (50 mL) was added to the mixture, and added saturated NaHCO3 solution to the mixture until pH=7, then extracted (ethyl acetate), washed (brine), dried (Na2SO4), concentrated to give 3-acetamidophenyl acetate as gray solid (30 g, yield: 93%). ESI-MS: 194 (M+H)+.

Workup

  1. extractionextracted (ethyl acetate)
  2. washwashed (brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40a45a694f4348df8dee984bcfc2ad7d
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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