Methyl 2-acetamido-3-chlorobenzoate → Benzoic acid, 2-amino-3-chloro-, methyl ester

HRID 974415Notes

Reaction equation

HRID 974415 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[NH:12]C(=O)C)([O:3][CH3:4])=[O:2]>CO>[Cl:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([O:3][CH3:4])=[O:2])[C:6]=1[NH2:12]

Participants

3

Reactant 1

HCID 15027235Methyl 2-acetamido-3-chlorobenzoate

Product 1

HCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 0.1 g (2.3 mmole) of N-(2-carbomethoxy-6-chlorophenyl)acetamide in 10 mL of methanol containing 0.2 mL of conc. H2S04 was heated at reflux for ca. 18 hr. The methanol was removed in vacuo and the residue treated with 5 mL of EtOAc and 5 mL of H2O respectively. The phases were mixed and separated. The aqueous layer was extracted with 2×5 mL of EtOAc and the combined EtOAc solution dried (Na2SO4), filtered, and the solvent removed from the filtrate in vacuo. The product was purified by preparative thin layer chromatography (TLC) using 9:1 (v/v) CH2Cl2EtOAc. The band containing product was extracted with EtOAc and filtered. The solvent was removed from the filtrate in vacuo to afford 78 mg (91% yield) of methyl 3-chloroanthranilate as a light yellow solid: 1H NMR (CDCl3, TMS) δ7.80 (d, 8 Hz, H6), 7.39 (d, 8 Hz, H4), 6.55 (t, 8 Hz, H5), 6.25 (broad s, NH2), 3.90 (s, OCH3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for ca. 18 hr
  3. customThe methanol was removed in vacuo
  4. additionthe residue treated with 5 mL of EtOAc and 5 mL of H2O respectively
  5. additionThe phases were mixed
  6. customseparated
  7. extractionThe aqueous layer was extracted with 2×5 mL of EtOAc
  8. dry with materialthe combined EtOAc solution dried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent removed from the filtrate in vacuo
  11. customThe product was purified by preparative thin layer chromatography (TLC)
  12. additionThe band containing product
  13. extractionwas extracted with EtOAc
  14. filtrationfiltered
  15. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-511ec4e1a5fe493591be9ab85cdb92e7
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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