Acetyl chloride → Methyl 4-Amino-2-chlorobenzoate

HRID 2038434Notes

Reaction equation

HRID 2038434 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 (2.5 mL, 35.2 mmol) was added dropwise to a stirring solution of 4-amino-2-chloro-benzoic acid 22i (2.22 g, 12.9 mmol) in methanol (50 mL). The mixture was heated at reflux for 18 h, cooled, and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed sequentially with saturated aqueous NaHCO3 and brine, dried, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexanes) to give compound 22j.

Workup

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

Sources & evidence

ORD record
ord-02841138ee414692968802c5b210e3c0
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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