Iodine → Methyl 2-amino-4-chloro-5-iodobenzoate

HRID 1672180Notes

Reaction equation

HRID 1672180 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:3][C:4]1[CH:13]=[C:12]([Cl:14])[C:11]([I:1])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 807IodineHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoateYield 101.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a mixture of iodine (68 g, 0.27 mol) and silver sulfate (84 g, 0.27 mol) in absolute EtOH (2.5 L) was added methyl 2-amino-4-chlorobenzoate (50 g, 0.27 mol). The reaction mixture was allowed to stir at rt for 45 min. The reaction mixture was then filtered through a pad of Celite® and the filtrate was concentrated. The residue was dissolved in EtOAc (2 L) and washed with saturated aqueous NaHCO3 (3×400 mL), water (3×400 mL), and brine. The organic solution was dried over Na2SO4, filtered, and concentrated to give methyl 2-amino-4-chloro-5-iodobenzoate (85 g, 99%).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in EtOAc (2 L)
  4. washwashed with saturated aqueous NaHCO3 (3×400 mL), water (3×400 mL), and brine
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-66908aa0cc584167b08fdb5589368905
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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