Potassium Iodide → HCID 18319225, compound

HRID 1701001Notes

Reaction equation

HRID 1701001 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[C:4]([CH3:16])[CH:3]=1.N([O-])=O.[Na+].[I-:21].[K+]>Cl.O>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([I:21])=[CH:3][C:4]=2[CH3:16])=[CH:9][CH:10]=1)#[N:15]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 18319307HCID 18319307, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18319225HCID 18319225, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A suspension of 4-amino-1-(4-cyanophenyl)-2-methylbenzene (250 mg 1.2 mmol) in conc. hydrochloric acid (1.3 mL) and water (1.6 mL) at 0° C., was treated with a solution of sodium nitrite (183 mg, 2.65 mmol) in water (1 mL) over 10 mins. The mixture was stirred for 20 mins and then a solution of potassium iodide (840 mg, 5.06 mmol) in water (2 mL) was added, over 10 mins. The resultant mixture was heated at 90° C. for 2 h, then cooled. The residue was extracted with dichloromethane (3×30 mL) and the combined organic extracts were washed with 5% aqueous sodium metabisulphite (4×30 mL), to remove iodine. The organic solution was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 10:1) to give 1-(4-cyanophenyl)-4-iodo-2-methylbenzene as a white solid (263 mg, 69%).

Workup

  1. temperaturecooled
  2. extractionThe residue was extracted with dichloromethane (3×30 mL)
  3. washthe combined organic extracts were washed with 5% aqueous sodium metabisulphite (4×30 mL)
  4. customto remove iodine
  5. dry with materialThe organic solution was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (gradient elution with hexane:ethyl acetate 20:1 to 10:1)

Sources & evidence

ORD record
ord-54b5bbb37b8446ed85707e74d277cad0
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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