Sodium Hydroxide → 3-Iodo-5-(trifluoromethyl)pyridin-2-amine

HRID 1948627Notes

Reaction equation

HRID 1948627 reaction equation
[I:1][C:2]1[C:3]([NH:12]C(=O)C(C)(C)C)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[I:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 49761587HCID 49761587, compound

Product 1

HCID 153509143-Iodo-5-(trifluoromethyl)pyridin-2-amineYield 100.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(3-iodo-5-(trifluoromethyl)pyridin-2-yl)pivalamide (16.8 g, 45.1 mmole) was taken up in H2SO4 (24 wt. %, 392 ml) and the mixture was stirred for 60 minutes under reflux. After cooling to RT the mixture was neutralised with 4 N NaOH and solid NaHCO3, the aqueous phase was extracted with DCM (3×200 ml) and the combined organic phases were dried over MgSO4. After filtration the solvent was removed on a rotary evaporator. 3-iodo-5-(trifluoromethyl)pyridin-2-amine (13 g, 100%) was obtained as a cream-coloured solid.

Workup

  1. temperatureunder reflux
  2. extractionthe aqueous phase was extracted with DCM (3×200 ml)
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. filtrationAfter filtration the solvent
  5. customwas removed on a rotary evaporator

Sources & evidence

ORD record
ord-d4e8c0d6cc0b457aa6c500f0bd61869e
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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