Ethyl Acetate → 6-Chloro-2-iodo-4-methylpyridin-3-amine

HRID 887711Notes

Reaction equation

HRID 887711 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[I:10]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C=O)C>[NH2:1][C:2]1[C:7]([I:10])=[N:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 27344253-Amino-6-chloro-4-picoline

Product 1

HCID 593552676-Chloro-2-iodo-4-methylpyridin-3-amineYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-2-chloro-4-methylpyridine (1.35 g) was dissolved in DMF (20 mL), N-iodosuccinimide (2.59 g) was added and the reaction mixture was stirred at room temperature for 12 hours. Ethyl acetate was added and the organic layer was washed 3× with water, washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.30) to afford 1.38 g of the title compound of the formula

Workup

  1. washthe organic layer was washed 3× with water
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.30)

Sources & evidence

ORD record
ord-826adc0d7a094bf4970cde8ee6e16a91
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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