Sulfuric Acid → 3-Iodo-4-methyl-2-nitrobenzoic acid

HRID 2092278Notes

Reaction equation

HRID 2092278 reaction equation
N[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:24].[K+]>CS(C)=O.O>[I:24][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 50773353-Amino-4-methyl-2-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 529879563-Iodo-4-methyl-2-nitrobenzoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Amino-4-methyl-2-nitrobenzoic acid (13 g, 66 mmol) was taken up in 50 mL of DMSO and 30% aqueous sulfuric acid (150 mL) was added. The mixture was cooled to 0° C. and sodium nitrite (7 g, 99 mmol) dissolved in 20 mL of water was added slowly. The mixture was stirred for 1 h and potassium iodide (28 g, 166 mmol) dissolved in 50 mL of water was added. The mixture was allowed to stir at RT for 1 h. The mixture was extracted with ethyl acetate and the organic layer washed with an aqueous solution of 2 M sodium sulfite, water and brine. The organic layer was dried with sodium sulfate and concentrated under vacuum to give 3-iodo-4-methyl-2-nitrobenzoic acid (17 g, 84%) as a light brown solid. MS (M+H)+ 308.

Workup

  1. additionwas added slowly
  2. additionwas added
  3. stirringto stir at RT for 1 h
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer washed with an aqueous solution of 2 M sodium sulfite, water and brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-36985546d90a4bf08e338e147874c5a5
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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