Iodine → 4-(4-Iodobenzyl)pyridine

HRID 1994150Notes

Reaction equation

HRID 1994150 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[CH:14]=[CH:13][C:11](N)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.N([O-])=O.[Na+].[I:19]I>C(O)(=O)C.Cl.O>[I:19][C:11]1[CH:13]=[CH:14][C:8]([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 807IodineHCID 3071584-[(Pyridin-4-yl)methyl]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 147430304-(4-Iodobenzyl)pyridineYield 21.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 4-(pyridin-4-ylmethyl)aniline (679 mg, 3.7 mmol) in acetic acid (1.84 mL) and concentrated hydrochloric acid (0.787 mL) was cooled to 0° C. NaNO2 (280 mg, 40.7 mmol) in water (1.23 mL) was added dropwise and the reaction mixture was allowed to stir for 30 min. A solution of KI (737 mg, 4.44 mmol) and iodine (563 mg, 2.22 mmole) in water (3.7 mL) was added dropwise to the above solution. The solution stirred for 30 min at 0° C. and for 1 h at rt. The reaction was quenched by the addition of aq. NaS2O4 and the solution was extracted with EtOAc. The combined organic solutions were washed with sat. NaHCO3, brine and 1% NaOH, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give the title compound (140 mg, 18%). LCMS: (FA) ES+ 296.1 (M+1).

Workup

  1. stirringThe solution stirred for 30 min at 0° C. and for 1 h at rt
  2. customThe reaction was quenched by the addition of aq. NaS2O4
  3. extractionthe solution was extracted with EtOAc
  4. washThe combined organic solutions were washed with sat. NaHCO3, brine and 1% NaOH
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4c3693158ffc4e5eb13d6e263906c3c4
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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