2-Pyridinamine, 5-iodo- → 5-Phenoxypyridin-2-amine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux under a nitrogen atmosphere for 24 hours
- customThe solvent is removed in vacuo
- extractionthe residue is extracted with chloroform
- 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
Reaction notes
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