2-Pyridinamine, 5-iodo- → HCID 43144875, compound

HRID 614847Notes

Reaction equation

HRID 614847 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O-:7])[CH:2]=1.[K+].[NH2:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]=1>CC(N(C)C)=O>[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 23663322HCID 23663322, compound

Product 1

HCID 43144875HCID 43144875, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3.3 G. of potassium 3-pyridinolate, 5.47 g. of 2-amino 5-iodopyridine and 1.78 g. of cuprous oxide in 150 ml. of dimethylacetamide are heated at reflux under a nitrogen atmosphere for 24 hours. The solvent is removed in vacuo and the residue is extracted with chloroform. Chromatography of the methylene chloride soluble portion with silica gel and elution with ethyl acetate yields 2-amino-5-(3-pyridyloxy) pyridine.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 24 hours
  2. customThe solvent is removed in vacuo
  3. extractionthe residue is extracted with chloroform
  4. washChromatography of the methylene chloride soluble portion with silica gel and elution with ethyl acetate

Sources & evidence

ORD record
ord-da16c0f3c4d344afa3daa26a7e35d28c
Source dataset
uspto-grants-1979_03
Patent number
US04146642

Reaction notes

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