Pyridine → (3-Acetamidophenyl) acetate

HRID 709851Notes

Reaction equation

HRID 709851 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-678acc2b0cc1445ca528089e42f4b2a3
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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