Reaction #7872

Reaction equation

3-aminopyridine

triethylamine

trimethylacetyl chloride

→

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

Solvents

CH2Cl2

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated in vacuo
2. 2
   Otherthe residue partitioned between EtOAc and H2O
3. 3
   Otherthe layers separated
4. 4
   Extractionextracted with EtOAc
5. 5
   WashThe combined organic layers were washed with saturated NaHCO3 and brine
6. 6
   Dryingdried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo

Procedure

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).

Source