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

HRID 2098023Notes

Reaction equation

HRID 2098023 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-03571526ee024c908bc7ea4ccfda9077
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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