Iodine → 2-Iodo-6-(trifluoromethyl)pyridin-3-amine

HRID 1519811Notes

Reaction equation

HRID 1519811 reaction equation
[I:1]I.[F:3][C:4]([F:13])([F:12])[C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:9]1[C:8]([NH2:11])=[CH:7][CH:6]=[C:5]([C:4]([F:3])([F:12])[F:13])[N:10]=1

Participants

5

Reactant 2

HCID 807IodineHCID 27377445-Amino-2-(trifluoromethyl)pyridine

Product 1

HCID 534254792-Iodo-6-(trifluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (7.83 g, 30.84 mmol) and silver sulfate (9.6 g, 30.84 mmol) were added to a solution of 6-(trifluoromethyl)pyridin-3-amine (5 g, 30.84 mmol) in ethanol (200 ml) and the resulting suspension was stirred at room temperature for 18 h. the solution was filtered and the filtrate was concentrated under vacuum. The residue was re-dissolved in methylene chloride and washed with aqueous NaOH (1 N), dried (Na2SO4), filtered and concentrated under vacuum to give 2-iodo-6-(trifluoromethyl)pyridin-3-amine. Retention time (min)=2.136, method [1], MS(ESI) 289.01 (M+H).

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe residue was re-dissolved in methylene chloride
  4. washwashed with aqueous NaOH (1 N)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4f5974e2feb4e01af207e4e56d4df7f
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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