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

HRID 839635

Reaction equation

HRID 839635 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-eaa44ef71d95469786d79e2ca79f7d0d
Source dataset
uspto-grants-1978_06
Patent number
US04096264

Linked notes

Loading…