Lithium iodide → 2-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid

HRID 1945438Notes

Reaction equation

HRID 1945438 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]([Br:20])=[CH:16][C:15]=2[Cl:21])[CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=2)[C:3]([OH:23])=[O:2])=[O:22])=[C:15]([Cl:21])[CH:16]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 248120962-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester

Product 1

HCID 580013432-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acidYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[2-(4-bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester (50 mg, 0.125 mmol) and lithium Iodide (189 mg, 1.25 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-(4-bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid as a colorless solid (0.012 g, 25% 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-4dd6ec5d58e44a21a28c88685105e6c9
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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