반응 #7872

반응 방정식

3-aminopyridine

triethylamine

trimethylacetyl chloride

→

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

용매

CH2Cl2

반응 조건

후처리

1. 1
   농축The mixture was concentrated in vacuo
2. 2
   기타the residue partitioned between EtOAc and H2O
3. 3
   기타the layers separated
4. 4
   추출extracted with EtOAc
5. 5
   세척The combined organic layers were washed with saturated NaHCO3 and brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

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).

출처