Potassium Iodide → HCID 18319289, compound

HRID 1701004Notes

Reaction equation

HRID 1701004 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[C:4]([CH3:16])[CH:3]=1.N([O-])=O.[Na+].[I-:21].[K+]>Cl.O>[C:14]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([I:21])=[CH:3][C:4]=2[CH3:16])[CH:13]=[CH:12][CH:11]=1)#[N:15]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 18319266HCID 18319266, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18319289HCID 18319289, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A suspension of 4-amino-l-(3-cyanophenyl)-2-methylbenzene (2.5 gm, 12.0 mmol) in conc. hydrochloric acid (13 mL) and water (16 mL) at 0° C., was treated with a solution of sodium nitrite (1.83 gm, 26.5 mmol) in water (10 mL) over 10 mins. The mixture was stirred for 20 mins and then a solution of potassium iodide (8.40 gm, 50.6 mmol) in water (20 mL) was added over 10 mins. The resultant mixture was heated at 80° C. for 2 h then cooled. The residue was extracted with dichloromethane and the combined organic extracts were washed with excess 5% aqueous sodium metabisulphite, 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-(3-cyanophenyl)-4-iodo-2-methylbenzene as a white solid (1.105 gm, 29%).

Workup

  1. temperaturethen cooled
  2. extractionThe residue was extracted with dichloromethane
  3. washthe combined organic extracts were washed with excess 5% aqueous sodium metabisulphite
  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-c75e7643a2ef4a3cba7872f698e7bbfa
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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