Reacción #1321

Ecuación de reacción

6-iodonicotinic acid

ethanol

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

→

title compound

Ethyl 6-iodonicotinoate

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   Otropartitioned between 200 ml of water and 250 ml of ethyl ether
3. 3
   Otrothe layers were separated
4. 4
   LavadoThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
5. 5
   Lavadowashed once with 75 ml of brine solution
6. 6
   Secadodried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo to a yellow solid
9. 9
   OtroPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Procedimiento

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.

Fuente