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

HRID 875409Notes

Reaction equation

HRID 875409 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-bc0028780b2d4f4a88afc0154b1459ad
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

Loading…