2-chloro-N-(2,4-dimethoxyphenyl)acetamide → 2-Chloroacetamido-5-methoxy phenol

HRID 38411Notes

Reaction equation

HRID 38411 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14]C)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[OH:14])=[O:4]

Participants

4

Reactant 2

HCID 3038242-chloro-N-(2,4-dimethoxyphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135065532-Chloroacetamido-5-methoxy phenolYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-N-(2,4-dimethoxy-phenyl)-acetamide (45.8 g, 0.2 mol) was dissolved in 1000 mL methylene chloride, and the reaction mixture was stirred at 0° C. under nitrogen. Aluminum trichloride (78.9 g, 0.6 mol) was added in portions over 30 minutes, and the reaction mixture was allowed to stir for 17 hours at room temperature. The reaction mixture was concentrated to 200 mL volume under reduced pressure, and then poured onto ice. Solids were removed by filtration, and the liquid was taken up in EtOAc, washed with brine, dried (MgSO4), filtered, and evaporated under reduced pressure to yield 39.67 g of 2-Chloro-N-(2-hydroxy-4-methoxy-phenyl)-acetamide. MS (M+H)=216.

Workup

  1. stirringto stir for 17 hours at room temperature
  2. concentrationThe reaction mixture was concentrated to 200 mL volume under reduced pressure
  3. additionpoured onto ice
  4. customSolids were removed by filtration
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1df77548902c412289a0d4218c428ab1
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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