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

HRID 2419313Notes

Reaction equation

HRID 2419313 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-a173122d37434d3ba61f47e525daf874
Source dataset
uspto-grants-1978_08
Patent number
US04105767

Reaction notes

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