Reaktion #345308

Reaktionsgleichung

Ether

ethanol

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

6-iodo-nicotinic acid

→

title compound

Ethyl 6-Iodo-nicotinoate

Lösungsmittel

water

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for 12 hours
2. 2
   Sonstigethe layers separated
3. 3
   ExtraktionThe aqueous layer was extracted with 2×40 ml of ether
4. 4
   Waschenwashed with saturated NaCl
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   Sonstigeyielding a white solid which
8. 8
   Sonstigewas purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

Vorschrift

A mixture of 16.230 g (84.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 90 ml of methylene chloride was cannulated into a mixture of 17.80 g (71.2 mmol) of 6-iodo-nicotinic acid in 30 ml of methylene chloride. The resulting mixture was stirred and 7.85 g (0.171 mmol) of ethanol, and then 0.826 g (6.8 mmol) of 4-dimethylaminopyridine was added and the resulting mixture refluxed at 55° C. for 20 hours and then stirred at room temperature for 12 hours. Ether and water were added and the layers separated. The aqueous layer was extracted with 2×40 ml of ether and the organic portions combined, washed with saturated NaCl, dried over Na2SO4, and concentrated yielding a white solid which was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give the title compound as a white solid.

Quelle