Iodine → 2-Iodo-4-methylaniline

HRID 370357

Reaction equation

HRID 370357 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[I:14]I>C(Cl)Cl.O>[I:14][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 807IodineHCID 7813p-ToluidineHCID 516892Sodium Bicarbonate

Product 1

HCID 27640002-Iodo-4-methylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of p-toluidine (5 g, 46.7 mmol) in methylene chloride (25 mL) was added a solution of sodium bicarbonate (4.7 g, 56 mmol) in water (75 mL). Then was added iodine (11.26 g, 44.33 mmol) in small portions and the mixture was stirred for 16 hours at room temperature. The reaction was quenched with saturated NaHSO3 and the product was extracted with methylene chloride. The methylene chloride layer was washed with brine, dried over Na2SO4, and evaporated in vacuo to give a crude 2-iodo-4-methylaniline.

Workup

  1. customThe reaction was quenched with saturated NaHSO3
  2. extractionthe product was extracted with methylene chloride
  3. washThe methylene chloride layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-03feabe7ed0f49ca985286056400081a
Source dataset
uspto-grants-2000_10
Patent number
US06140499

Linked notes

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