Ethyl 2-ethylnicotinate synthesis
- Product Name:Ethyl 2-ethylnicotinate
- CAS Number:3197-39-5
- Molecular formula:C10H13NO2
- Molecular Weight:179.22
Yield: 61%
Reaction Conditions:
Stage #1:diethylzinc;ethyl 2-chloronicotinate;palladium bis[bis(diphenylphosphino)ferrocene] dichloride in 1,4-dioxane;toluene at 20 - 70; for 1 h;
Stage #2: with methanol in 1,4-dioxane;toluene
Steps:
139
To a solution of ethyl 2-chloropyridine-3-carboxylate (15 g, 81 mmol) in anhydrous 1 ,4-dioxane (150 mL) at room temperature was added (1,1'- bis(diphenylphosphino)ferrocene) dichloropalladium (II) (1.3 g, 1.6 mmol) followed by a diethylzinc solution (75 mL, 83 mmol, 1.1 M solution in toluene). The mixture was stirred at 700C for 1 hour. After cooling to room temperature, the reaction was quenched with MeOH. Ethyl acetate (200 mL) was added. The mixture was extracted with 0.2 N HCl (200 mL). The organic layer was recovered. The pH of the aqueous phase was brought around 6 with 2 N NaOH. The mixture was extracted with EtOAc (1 x 100 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-20% ethyl acetate/hexane), affording ethyl 2-ethylpyridine-3- carboxylate (8.8 g, 61% yield)
References:
CHLORION PHARMA, INC.;UNIVERSITE LAVAL;ATTARDO, Giorgio;TRIPATHY, Sasmita WO2010/132999, 2010, A1 Location in patent:Page/Page column 200-201
