Pyridine → (3-Acetamidophenyl) acetate

HRID 709894Notes

Reaction equation

HRID 709894 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 0.17 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 saturated NaHCO3 solution was added to the mixture until pH=7, then extracted (EA), washed (brine), dried (Na2SO4), and concentrated to give 3-acetamidophenyl acetate as gray solid (30 g, yield: 93%). ESI-MS: 194 (M+H)+.

Workup

  1. additionwas added to the mixture until pH=7
  2. extractionextracted (EA)
  3. washwashed (brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac5a3386b606437b9357d197b8b9f49f
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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