4-Ethylpyridin-2-amine → 4-Ethyl-5-iodopyridin-2-amine

HRID 1502150Notes

Reaction equation

HRID 1502150 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=1)[CH3:10]>CC(O)=O>[CH2:9]([C:11]1[C:16]([I:1])=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=1)[CH3:10]

Participants

4

Reactant 2

HCID 1184254-Ethylpyridin-2-amineHCID 120273N-Iodosuccinimide

Product 1

HCID 582005784-Ethyl-5-iodopyridin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

1-Iodopyrrolidine-2,5-dione (NIS, 3.87 g, 17.2 mmol) was added in portions to 4-ethylpyridin-2-amine (2.00 g, 16.4 mmol) in AcOH (60 m) during 30 min at 65° C. The mixture was heated at 65° C. for 36 hours, was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane 25 to 40%) to provide 4-ethyl-5-iodopyridin-2-amine: LC-MS: [(M+1)]+=249.00

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane 25 to 40%)

Sources & evidence

ORD record
ord-2f1685be1da44b4eb45e5355ff885f3e
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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