Acetyl chloride → Methyl 4-Amino-2-chlorobenzoate

HRID 403314Notes

Reaction equation

HRID 403314 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-92eea13584c740f5838cd843e5ccb51b
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

Loading…