Diiodomethane → 2-Iodo-4-methyl-5-nitropyridine

HRID 34065

Reaction equation

HRID 34065 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.S([O-])(OCCC(C)C)=O.[I:21]CI>>[I:21][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 2431652-Amino-4-methyl-5-nitropyridineHCID 22742080Isopentyl sulfite

Product 1

HCID 230701672-Iodo-4-methyl-5-nitropyridine

Conditions

Temperature
80 °C

Procedure

To a solution of 1.0 g of 2-amino-4-methyl-5-nitropyridine in 10 mL of diiodomethane was added 1.8 mL of isopentyl sulfite at room temperature, stirred at this temperature for 30 minutes, and after raising the temperature to 80° C., the solution was stirred for 2 hours. The diiodomethane was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20), to afford 897 mg of the title compound as colorless crystals.

Workup

  1. stirringthe solution was stirred for 2 hours
  2. customThe diiodomethane was evaporated
  3. customthe crude product was purified
  4. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:20)

Sources & evidence

ORD record
ord-4591426222324116a52532a1d4076497
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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