N-(2,6-dichloro-3,5-dimethoxyphenyl)acetamide → 2,6-Dichloro-3,5-dimethoxyaniline

HRID 409656Notes

Reaction equation

HRID 409656 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13]C(=O)C>C(O)C.[OH-].[K+]>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 56594869N-(2,6-dichloro-3,5-dimethoxyphenyl)acetamide

Product 1

HCID 594862532,6-Dichloro-3,5-dimethoxyaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of N-(2,6-dichloro-3,5-dimethoxy-phenyl)-acetamide (34.5 g, 264 mmol) in ethanol (1.3 L), 2M KOH (0.72 L) is added. Then, the reaction mixture is heated to reflux, stirred for 44 h at reflux, then allowed to cool to RT. The resulting suspension is cooled to 0° C. stirred for 1 h, and filtered. The residue is washed with a small portion of cold EtOH/H2O (1:1) and with cold H2O till neutrality, and dried to provide the title compound as a white solid: ESI-MS: 222.0/224.0 [MH]+, TLC: Rf=0.52 (Hex/EtOAc, 1:1).

Workup

  1. temperatureThen, the reaction mixture is heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureThe resulting suspension is cooled to 0° C.
  5. stirringstirred for 1 h
  6. filtrationfiltered
  7. washThe residue is washed with a small portion of cold EtOH/H2O (1:1) and with cold H2O till neutrality, and
  8. customdried

Sources & evidence

ORD record
ord-459889283d0a45acaff1e0d8736a9981
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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