2-Pyridinamine, 5-iodo- → 5-Phenoxypyridin-2-amine

HRID 1447609Notes

Reaction equation

HRID 1447609 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][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:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 23670670Potassium phenoxide

Product 1

HCID 221794545-Phenoxypyridin-2-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3.3 G. of potassium phenolate, 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-phenoxy pyridine m.p. 67°-69° C.

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-4a7397b39b674ea7aa25910a58bb2738
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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