Potassium Iodide → 3-Iodo-5-(trifluoromethyl)pyridin-2-amine

HRID 1515909Notes

Reaction equation

HRID 1515909 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[I:12]([O-])(=O)=O.[K+].[I-].[K+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[I:12][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 23665710Potassium Iodate

Product 1

HCID 153509143-Iodo-5-(trifluoromethyl)pyridin-2-amineYield 227.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-trifluoromethyl-pyridin-2-ylamine (32.4 g, 0.2 mol) and potassium iodate (17.12 g, 0.08 mol) in 2M sulfuric acid (400 mL) was heated at 100° C. and a solution of potassium iodide (33.2 g, 0.2 mol) in water (83 mL) was added dropwise over 1 h. The resulting mixture was heated to reflux for 12 h. After being cooled to room temperature, the mixture was adjusted to pH 7 with careful addition of solid sodium bicarbonate. The mixture was extracted with dichloromethane, washed with a saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-iodo-5-trifluoromethyl-pyridin-2-ylamine (52.5 g, 91%) as yellow solid: LC/MS m/e calcd for C4H3IN2 [M+H]+ 289.01, observed 288.8.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 12 h
  3. temperatureAfter being cooled to room temperature
  4. extractionThe mixture was extracted with dichloromethane
  5. washwashed with a saturated sodium thiosulfate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaecd08ba2bd4584bc734d63d8dc9f34
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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