Sodium Iodide → HCID 68511944, compound

HRID 643012Notes

Reaction equation

HRID 643012 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[N:6][CH:7]=1.N([O-])=O.[Na+].[Na+].[I-:20]>Cl.O>[I:20][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 23339834HCID 23339834, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 68511944HCID 68511944, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1-(5-aminopyridin-2-yl)pyridin-2(1H)-one (316 mg, 1.69 mmol) in concentrated HCl (8 mL) cooled in an ice bath, a solution of NaNO2 (117 mg, 1.69 mmol) in H2O (3 mL) was added dropwise. After 30 min of stirring, NaI (1.03 g, 6.87 mmol) in H2O (4 mL) was added. The mixture was stirred at 0° C. for 1 h. It was then allowed to warm up to room temperature and stirred at room temperature overnight. The mixture was extracted with EtOAc. The EtOAc solution was washed with 5% NaHCO3, then with Na2S2O3, dried over Na2SO4, and concentrated in vacuo to give 1-(5-iodopyridin-2-yl)pyridin-2(1H)-one (189 mg).

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. stirringstirred at room temperature overnight
  3. extractionThe mixture was extracted with EtOAc
  4. washThe EtOAc solution was washed with 5% NaHCO3
  5. dry with materialwith Na2S2O3, dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0776874158894de2a9363f844b8c8eba
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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