546 Dr Sell, Chlorination of a-Picoline. 



Further study of the Products of Chlorination of a-Picoline. 

 By Dr Sell. 



[Bead 23 May 1910.] 



One of the most important compounds obtained by the 



CI 



. . . . , . , Cl^^Cl 



chlormation of a-picoline has the formula . This 



^ H\ /'CCL 



substance has been shown to produce by the action of sulphuric 

 acid besides 3. 4. 5. trichloropicolinic acid and 3. 4. 5. trichlo- 

 ropyridine formerly described, a small quantity of an acid 

 regarded as 8 oxy 4. 5. dichloropicolinic acid. This compound 

 is resolved by heat into the corresponding oxydichloropyridine. 



The above hexachloropicoline also reacts with alcoholic sodium 

 hydroxide and yields 4 oxy 3. 5. dichloropicolinic acid, resolved by 

 heat into 4 oxy 3. 5. dichloropyridine isomeric with the last- 

 mentioned oxydichloi'opyridine. 



It is also found that 3. 4. 5. trichloropicolinic acid gives with 

 ammonia 4 amino 3. 5. dichloropicolinic acid which by heat is 

 resolved into 4 amino 3. 5. dichloropyridine, and the same com- 

 pound is also formed from 3. 4. 5. trichloropyridine by heating 

 with ammonia. Finally when the amino group in 4 amino 8. 6. 

 dichloropyridine is replaced by the hydroxyl group the same 

 oxydichloropyridine is obtained as was shown to be produced by 

 alcoholic sodium hydroxide on the original hexachloropicoline and 

 heating the oxydichloropicolinic acid thus produced. 



