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

HRID 450324Notes

Reaction equation

HRID 450324 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.CC(O)=O>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) is stirred in 6 M aq. HCl-solution (120 mL) and AcOH (250 mL) at reflux for 24 h. The reaction mixture is cooled, concentrated, diluted with water and concentrated again. The residue is diluted with water, stirred under cooling and filtered. The filtercake is washed and dried to give the sub-title compound.

Workup

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

Sources & evidence

ORD record
ord-168851a852f84aeca4aa3be26c600c28
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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