Reacción #7872

Ecuación de reacción

3-aminopyridine

triethylamine

trimethylacetyl chloride

→

N-(pyridin-3-yl)-2,2-dimethylpropanamide

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated in vacuo
2. 2
   Otrothe residue partitioned between EtOAc and H2O
3. 3
   Otrothe layers separated
4. 4
   Extracciónextracted with EtOAc
5. 5
   LavadoThe combined organic layers were washed with saturated NaHCO3 and brine
6. 6
   Secadodried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

To a stirred solution of 3-aminopyridine (9.41 g, 100 mmol) and triethylamine (16.7 mL, 120 mmol) in CH2Cl2 (300 mL) at 0° C. was added trimethylacetyl chloride (14.8 mL, 120 mmol) dropwise over 15 min. The reaction was warmed to rt and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned between EtOAc and H2O, and the layers separated. The aqueous layer was made basic with saturated NaHCO3 and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-(pyridin-3-yl)-2,2-dimethylpropanamide as a tan solid. 1H NMR (CDCl3, 300 MHz) δ 8.57 (d, 1H), 8.33 (dd, 1H), 8.17 (ddd, 1H), 7.69 (br s, 1H), 7.27 (dd, 1H), 1.33 (s, 9H).

Fuente