Sulfuric Acid → 2-Iodo-4-nitrobenzoic acid

HRID 541758Notes

Reaction equation

HRID 541758 reaction equation
N[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:23].[K+]>O>[I:23][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 120764-Nitroanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 4589642-Iodo-4-nitrobenzoic acidYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2-amino-4-nitrobenzoic acid (14.5 g, 79.6 mmol) in 2.0 M of sulfuric acid aqueous solution (398 mL, 796 mmol) was added a solution of sodium nitrite (8.24 g, 0.119 mol) in water dropwise at 0° C. After the addition, the resulting solution was stirred at same temperature for 1 hour, then a solution of potassium iodide (19.8 g, 0.119 mol) in water was added dropwise at 0° C. The resulting mixture was stirred at rt for 72 hours. The precipitate was filtered and washed by water to give the desired product (19.5 g, 83%). LCMS calculated for C7H51NO4(M+H)+: m/z=294.0.

Workup

  1. additionAfter the addition
  2. stirringThe resulting mixture was stirred at rt for 72 hours
  3. filtrationThe precipitate was filtered
  4. washwashed by water

Sources & evidence

ORD record
ord-1fed4667015b45ea94fbdcd512d29e7e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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