تفاعل #46225

معادلة التفاعل

5-methylpyridin-2-amine

Et3N

2,2-dimethyl-propionyl chloride

→

2,2-dimethyl-N-(5-methyl-pyridin-2-yl)-propionamide

المردود 98.4%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice bath was removed
2. 2
   workup.ADDITIONThe reaction was poured into ice (2000 g)
3. 3
   أخرىThe organic layer was separated
4. 4
   استخلاصthe remaining aqueous layer was extracted with CH2Cl2 (3×)
5. 5
   تجفيفThe combined organics were dried over Na2SO4
6. 6
   أخرىevaporated

الإجراء التجريبي

To a stirred solution of 5-methylpyridin-2-amine (200 g, 1.85 mol) in anhydrous CH2Cl2 (1000 mL) was added dropwise a solution of Et3N (513 mL, 3.70 mol) and 2,2-dimethyl-propionyl chloride (274 mL, 2.22 mol) at 0° C. under N2. The ice bath was removed and stirring was continued at room temperature for 2 hours. The reaction was poured into ice (2000 g). The organic layer was separated and the remaining aqueous layer was extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4 and evaporated to afford 2,2-dimethyl-N-(5-methyl-pyridin-2-yl)-propionamide (350 g), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 1H), 8.06 (d, J=1.2 Hz, 1H), 7.96 (s, 1H), 7.49 (dd, J=1.6, 8.4 Hz, 1H), 2.27 (s, 1H), 1.30 (s, 9H).

المصدر