Acetic Acid → 3-Amino-2,4-dichlorobenzoic acid

HRID 1258646Notes

Reaction equation

HRID 1258646 reaction equation
C([NH:4][C:5]1[C:6]([Cl:15])=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=O)C.C(O)(=O)C>Cl>[NH2:4][C:5]1[C:6]([Cl:15])=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 198331103-Acetamido-2,4-dichlorobenzoic acid

Product 1

HCID 152782343-Amino-2,4-dichlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-Acetylamino-2,4-dichloro-benzoic acid (21.0 g, 84.6 mmol) was stirred in 6 M aq. HCl-solution (120 mL) and acetic acid (250 mL) at reflux for 24 h. The reaction mixture was cooled, concentrated, diluted with water and concentrated again. The residue was diluted with water, stirred under cooling and filtered. The filtercake was washed and dried to give the sub-title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additiondiluted with water
  4. concentrationconcentrated again
  5. additionThe residue was diluted with water
  6. temperatureunder cooling
  7. filtrationfiltered
  8. washThe filtercake was washed
  9. customdried

Sources & evidence

ORD record
ord-b48597ec34394e1e8283ebe92fde53a7
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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