Methyl iodide → 1-(2-Amino-3-methoxyphenyl)ethan-1-one

HRID 1710815Notes

Reaction equation

HRID 1710815 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[NH2:9][C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17](=[O:19])[CH3:18]>CN(C=O)C>[NH2:9][C:10]1[C:15]([O:16][CH3:3])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 205912'-Amino-3'-hydroxyacetophenone

Product 1

HCID 136911411-(2-Amino-3-methoxyphenyl)ethan-1-oneYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of nitrogen, methyl iodide (1.35 g, 10 mmol) and potassium carbonate (4.39 g, 320 mmol) were added to a solution of 2′-amino-3′-hydroxyacetophenone (960 mg, 6 mmol, TCI Europe) in DMF (6 ml). The reaction mixture was stirred for 1 h at r.t., during which time the color of the mixture changed from light brown to dark green. The mixture was then worked up by extraction with H2O/ethyl acetate, drying of the organic phase (Na2SO4), and evaporation of solvent. The title compound (960 mg, 92%) was isolated from the residue by column chromatography (silica gel, heptan/ethyl acetate=100/0-70/30).

Workup

  1. extractionThe mixture was then worked up by extraction with H2O/ethyl acetate
  2. dry with materialdrying of the organic phase (Na2SO4), and evaporation of solvent

Sources & evidence

ORD record
ord-0b0278f1ce8b4866908d04d138df1280
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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