Sodium Iodide → 3-(4-Iodophenyl)pyridine

HRID 2050960Notes

Reaction equation

HRID 2050960 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.N([O-])=O.[Na+].[I-:25].[Na+].C([O-])(=O)C.[Na+]>O.C(O)(=O)C>[I:25][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 4595224-(Pyridin-3-yl)anilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 126443563-(4-Iodophenyl)pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1.7 g (10 mmol) of 3-(4-aminophenyl)-pyridine [F. S. Tanaka et al.. J. Agric. Food Chem. 30, 957 (1982)], 17 ml of glacial acetic acid and 1.5 ml of trifluoroacetic acid was cooled in ice-water. Sodium nitrite. 0.8 g (11.4 mmol) was added in portions. After stirring for 15 minutes in ice-water and 15 minutes without cooling, 5 g of sodium iodide and 3 g of sodium acetate was added slowly with water cooling. The reaction mixture was diluted with 30 ml of water and stirred for 30 minutes. It was then partitioned between methylene chloride and 10% aqueous sodium carbonate solution. The organic phase was dried and evaporated and the residue was chromatographed over 20 g of silica gel using 10% (V/V) of ethyl acetate in methylene chloride. Crystallization from hexane yielded off-white crystals with m.p. 112°-115°.

Workup

  1. addition0.8 g (11.4 mmol) was added in portions
  2. temperaturewithout cooling
  3. customIt was then partitioned between methylene chloride and 10% aqueous sodium carbonate solution
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe residue was chromatographed over 20 g of silica gel using 10% (V/V) of ethyl acetate in methylene chloride
  7. customCrystallization from hexane yielded off-white crystals with m.p. 112°-115°

Sources & evidence

ORD record
ord-4e128241d5d64e5384a45117a0daf3f9
Source dataset
uspto-grants-1991_05
Patent number
US05015661

Reaction notes

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