Potassium Iodide → 3-Iodo-5-nitrobenzoic acid

HRID 1070402Notes

Reaction equation

HRID 1070402 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[I-:18].[K+]>O.S(=O)(=O)(O)O>[I:18][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 2393423-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 805803-Iodo-5-nitrobenzoic acidYield 73.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 3-amino-5-nitrobenzoic acid (5.0 g, 27.45 mmol) in water (23 mL) and conc. sulfuric acid (3.15 mL) was added at 0-5° C. sodium nitrite (1.89 g, 27.45 mmol), the mixture was stirred at this temp for 1 h, and potassium iodide (7.59 g, 45.75 mmol) was added. After stirring at room temperature for an additional 2 h, the mixture was extracted, washed with a 10% solution of sodium sulfite, followed by water, then brine, dried over magnesium sulfate, and concentrated to dryness. Purification by flash chromatography gave 5.88 g of 3-iodo-5-nitro-benzoic acid as a yellow solid.

Workup

  1. stirringAfter stirring at room temperature for an additional 2 h
  2. extractionthe mixture was extracted
  3. washwashed with a 10% solution of sodium sulfite
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1ef3e997ebca4742bf0051bf4a1d6ee8
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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