3-Hydroxyacetanilide → HCID 22722095, compound

HRID 1581681Notes

Reaction equation

HRID 1581681 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:12]([NH:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)(=[O:14])[CH3:13]>CC(N(C)C)=O.[Cu-]=O>[C:12]([NH:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 121243-HydroxyacetanilideHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 22722095HCID 22722095, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

To a stirred solution of methyl 2-iodobenzoate (10 g, 38.2 mmole) in dimethylacetamide (50 mL) was added 3-acetamidophenol (5 g, 33 mmole) and copper(I) oxide (2.5 g, 17 mmole), and the mixture was heated at reflux under argon (180° C. oil bath). After 24 h the reaction was cooled to RT and most of the solvent was distilled off. The remaining residue was purified by flash chromatography on silica gel (50% EtOAc/hexane) to give the crude title compound (4.95, 55%): MS (ES) m/e 286.2 (M+H)+. The title compound prepared in this way contained approximately 45% N,O-diarylated acetamidophenol as a contaminant: MS (ES) m/e 420.4 (M+H)+. The mixture was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter 24 h the reaction was cooled to RT and most of the solvent
  3. distillationwas distilled off
  4. customThe remaining residue was purified by flash chromatography on silica gel (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-1b1f33a9762048d4b8bf2650c870abff
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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