Réaction #1321

Équation de réaction

6-iodonicotinic acid

ethanol

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

Ethyl 6-iodonicotinoate

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated in vacuo
2. 2
   Autrepartitioned between 200 ml of water and 250 ml of ethyl ether
3. 3
   Autrethe layers were separated
4. 4
   LavageThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
5. 5
   Lavagewashed once with 75 ml of brine solution
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo to a yellow solid
9. 9
   AutrePurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Mode opératoire

To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution mixture was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed once with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white solid.

Source