反应 #355774

反应方程式

pivaloyl chloride

4-aminopyridine

triethylamine

water

→

product

2,2-Dimethyl-N-pyridin-4-yl-propionamide

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   workup.ADDITIONAfter addition
2. 2
   洗涤the CH2Cl2 layer was washed with dilute NaHCO3
3. 3
   干燥dried over Na2SO4
4. 4
   其他evaporated
5. 5
   其他to leave a light brown solid
6. 6
   其他Recrystallization from EtOAc/hexanes

实验过程

Following procedures generally taught in J. A. Turner, J. Org. Chem. 1983, 48, 3401-3408, a solution of pivaloyl chloride (13.5 mL, 110 mmol) in CH2Cl2 (20 mL) was slowly added to an ice-cold solution of 4-aminopyridine (9.41 g, 100 mmol) and triethylamine (17.4 mL, 125 mmol) in CH2Cl2 (150 mL). After addition was complete, the resulting mixture was warmed to room temperature and stirred for 2 h. The solution was poured into water, the CH2Cl2 layer was washed with dilute NaHCO3, dried over Na2SO4, and evaporated to leave a light brown solid. Recrystallization from EtOAc/hexanes afforded the product as a white crystal, which was collected by vacuum filtration (13.03 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=4.8 Hz, 2 H), 7.50 (d, J=4.8 Hz, 2 H), 7.44 (br s, 1 H), 1.33 (s, 9 H). MS (LR-APCI) calcd. for C10H15N2O (M+H) 179.1; found 179.1.

来源