Lithium iodide → 2-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acid

HRID 1945435Notes

Reaction equation

HRID 1945435 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:22])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:11]([NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=1)[C:3]([OH:23])=[O:2])=[O:22]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 24812094HCID 24812094, compound

Product 1

HCID 580013332-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acidYield 41.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester (50 mg, 0.14 mmol) and lithium Iodide (189 mg, 1.41 mmol) in pyridine (3 mL) was heated to reflux until reaction completion, then cooled and distilled off the solvent under reduced pressure. The residue was taken up in water, neutralized and extracted with methanol/MC mixture (10%). The combined extracts were washed with brine and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by HPLC (MeOH/MC=10%) to afford 2-[2-(2,4-dichloro-phenoxy)acetylamino]-isonicotinic acid as a colorless solid (0.02 g, 41% yield).

Workup

  1. temperatureto reflux until reaction completion
  2. temperaturecooled
  3. distillationdistilled off the solvent under reduced pressure
  4. extractionextracted with methanol/MC mixture (10%)
  5. washThe combined extracts were washed with brine and water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crude product was purified by HPLC (MeOH/MC=10%)

Sources & evidence

ORD record
ord-50fc904dfb2d408eb0cd0035fcd912a2
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

Loading…