Lithium iodide → 2,6-Dichloro-4-(methylcarbamoyl)benzoic acid

HRID 2201802Notes

Reaction equation

HRID 2201802 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:15])[NH:13][CH3:14])[CH:9]=[C:8]([Cl:16])[C:3]=1[C:4]([O:6]C)=[O:5].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:15])[NH:13][CH3:14])[CH:9]=[C:8]([Cl:16])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 71061695Methyl 2,6-dichloro-4-(methylcarbamoyl)benzoate

Product 1

HCID 710616332,6-Dichloro-4-(methylcarbamoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A well stirred mixture of methyl 2,6-dichloro-4-(methylcarbamoyl)benzoate (280 mg, 1 mmol, Step a) and anhydrous lithium iodide (429 mg, 3.2 mmol) in pyridine (3 mL) was heated under reflux for 3 hours. The reaction mixture was concentrated under vacuum to remove pyridine. The residue was acidified using ice-cooled dilute hydrochloric acid solution and partitioned with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum to obtain a solid that upon triturating with cold diethyl ether yielded pure 2,6-dichloro-4-(methylcarbamoyl)benzoic acid (200 mg, 75%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto remove pyridine
  5. temperaturecooled dilute hydrochloric acid solution
  6. custompartitioned with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customto obtain a solid that
  11. customupon triturating with cold diethyl ether yielded pure 2,6-dichloro-4-(methylcarbamoyl)benzoic acid (200 mg, 75%)

Sources & evidence

ORD record
ord-84d647545a7b4a7caee40f9bac04290b
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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