Potassium Iodide → 2-Iodo-3-methoxybenzoic acid

HRID 906096Notes

Reaction equation

HRID 906096 reaction equation
N[C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N([O-])=O.[Na+].[I-:17].[K+]>Cl.O>[I:17][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 2557202-Amino-3-methoxybenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 4582192-Iodo-3-methoxybenzoic acidYield 38%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To 2-amino-3-methoxybenzoic acid (1.00 g, 5.98 mmol) in 25% aqueous hydrochloric acid (8 ml) at 0° C. was added sodium nitrite (0.45 g, 6.50 mmol) in water (3 ml). This solution was added drop-wise to a solution of potassium iodide (15.8 g, 59.3 mmol) in water (60 ml) and allowed to warm to 25° C. then stirred for 16 h. The reaction mixture was quenched with 1 N aqueous sodium bicarbonate until the pH became basic. The solution was extracted with methylene chloride and the organic dried over sodium sulfate, filtered, and concentrated to give a purple oil. The residue was purified by column chromatography, eluting with 10% methanol in dichloromethane. Pure fractions were concentrated to afford (0.623 g, 38%) of 2-iodo-3-methoxybenzoic acid. MS (EI) for C8H7IO3: 279 (MH+).

Workup

  1. customThe reaction mixture was quenched with 1 N aqueous sodium bicarbonate until the pH
  2. extractionThe solution was extracted with methylene chloride
  3. dry with materialthe organic dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a purple oil
  7. customThe residue was purified by column chromatography
  8. washeluting with 10% methanol in dichloromethane
  9. concentrationPure fractions were concentrated

Sources & evidence

ORD record
ord-4f53e985f8d64ced827924d1a741f186
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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