Acetyl chloride → Methyl 4-Amino-2-chlorobenzoate

HRID 401728Notes

Reaction equation

HRID 401728 reaction equation
[C:1](Cl)(=O)C.[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Cl:15])[CH:7]=1>CO>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:1])=[O:11])=[C:8]([Cl:15])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 171544-Amino-2-chlorobenzoic acid

Product 1

HCID 11839197Methyl 4-Amino-2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (35.2 mmol, 2.5 mL) was added dropwise to a stirring solution of 4-amino-2-chloro-benzoic acid 70l (12.9 mmol, 2.22 g) in methanol (50 mL). The mixture was heated at reflux for 18 h, cooled, and concentrated under vacuum. The residue was taken up in EtOAc, washed with saturated aqueous NaHCO3 and brine, dried, and concentrated under vacuum. The crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexanes) to give compound 70m.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. concentrationconcentrated under vacuum
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-973b6e8b717e4619b36f24a908fa5693
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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