Reaction #81798

Reaction equation

hexane

Ethylamine

2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

→

title compound

Yield 76.2%

N-(2-Chloro-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide

Yield 76.2%

Solvents

xylene

ethyl acetate

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo and water
2. 2
   workup.ADDITIONadded to the residue
3. 3
   ExtractionThe product was extracted with ether
4. 4
   Dryingdried (sodium sulfate)
5. 5
   Concentrationconcentrated
6. 6
   Otherto give an oil
7. 7
   Otherformed
8. 8
   FiltrationThe solid was filtered
9. 9
   Otherdried

Procedure

Ethylamine (12.7 g) was added to a suspension of 21.0 g of the 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide in 150 ml of xylene in a steel bomb. The mixture was then heated in an oil bath to 165° C. for 6 hrs. and then stirred overnight at room temperature. The solvent was removed in vacuo and water added to the residue. The product was extracted with ether, dried (sodium sulfate) and concentrated to give an oil. This was dissolved in ethyl acetate followed by hexane at which time a precipitate formed. The solid was filtered and dried to give 16.5 g of the title compound, m.p. 122°-124° C.

Source