Water → 6-Chloro-2-iodopyridin-3-amine

HRID 887725Notes

Reaction equation

HRID 887725 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[I:9]N1C(=O)CCC1=O.O.CCOCC>CN(C=O)C>[NH2:1][C:2]1[C:7]([I:9])=[N:6][C:5]([Cl:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 793055-Amino-2-chloropyridineHCID 120273N-Iodosuccinimide

Product 1

HCID 184070436-Chloro-2-iodopyridin-3-amineYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-2-chloropyridine (3.0 g) was dissolved in DMF (40 mL), N-iodosuccinimide (5.25 g) was added and the reaction mixture was stirred at room temperature for 3 hours. Water and MTB-ether were added to the reaction mixture, the layers were separated 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 4.80 g of the title compound of the formula

Workup

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

Sources & evidence

ORD record
ord-43d732d3f95e4666bb8a5b3221c2df18
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

Loading…