반응 #162380

반응 방정식

water

4-methylpyridin-3-amine

2-chloro-N,N-diethylnicotinamide

sodium hydride

→

desired product

수율 84.9%

N,N-diethyl-2-[(4-methylpyridin-3-yl)amino]nicotinamide

수율 84.9%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도at reflux for 1 hour
3. 3
   온도to cool
4. 4
   추출The mixture was then extracted with ethyl acetate 3×
5. 5
   세척the combined organic extracts were washed with water, brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrate in vacuo
8. 8
   온도Upon cooling
9. 9
   기타the product crystallized
10. 10
    여과The crystalline solid was filtered off
11. 11
    세척washed with ether
12. 12
    기타dried

실험 절차

Into a 1-neck round-bottom flask was added 4-methylpyridin-3-amine (1.02 g, 0.00940 mol) and 2-chloro-N,N-diethylnicotinamide (2.00 g, 0.00940 mol) in 1,4-dioxane (20 mL), and then sodium hydride (0.94 g, 0.024 mol) was added. The reaction was heated at reflux for 1 hour. The mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate 3× and the combined organic extracts were washed with water, brine, dried over MgSO4, and concentrate in vacuo. Upon cooling, the product crystallized. The crystalline solid was filtered off, washed with ether and dried to give 2.27 g of the desired product. 1H NMR (300 MHz, CDCl3): δ 9.15 (s, 1H), 8.21-8.24 (m, 2H), 7.90 (br s, 1H), 7.47 (dd, 1H J1=7.5, J2=1.8 Hz), 7.11 (d, 1H, J=4.8 Hz), 6.75 (dd, 1H, J1=7.5, J2=5.1 Hz), 3.46-3.51 (m, 4H), 2.29 (s, 3H), 1.25 (t, 6H). MS [M+1]=285.

출처