丁醇 → 3,4'-BIPYRIDIN-2'-AMINE

HRID 40829

反应方程式

HRID 40829 反应方程式
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[N+]([O-])(O)=O.[NH2:18][C:19]([NH2:21])=N.[OH-].[Na+].[CH2:24](O)CCC>>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[CH:4]=[CH:3][N:18]=[C:19]([NH2:21])[CH:24]=2)[CH:8]=1

参与物

5

反应物 4

HCID 263丁醇HCID 10481硝酸胍HCID 14798二甲基对苯二胺二盐酸HCID 5670331-(3-吡啶基)-3-(二甲氨基)-2-丙烯-1-酮

产物 1

HCID 167414843,4'-BIPYRIDIN-2'-AMINE收率 85%

实验过程

3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (15.4 g, 0.088 mol), guanidine nitrate (10.7 g, 0.088 mol), and sodium hydroxide (3.5 g, 0.088 mol) were dissolved in n-butanol (120 mL). The mixture was heated to reflux with stirring and maintained for 16 hours. The reaction mixture was then cooled to room temperature. The solid was collected and washed with water (400 mL). The desired product was dried under vacuum for three days and 12.7 g of yellow crystals of desired product was obtained (yield: 85%); 1H NMR (500 MHz, CDCl3) δ 5.15 (br., 2H), 7.09 (d, 1H), 7.44 (m, 1H), 8.33 (d, 1H), 8.42 (d, 1H), 8.73 (d, 1H), 9.22 (s, 1H). LC-MS (m/z) calculated, 172.2, found 173.2 [M+H]+.

后处理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained for 16 hours
  4. customThe solid was collected
  5. washwashed with water (400 mL)
  6. dry with materialThe desired product was dried under vacuum for three days

来源与证据

ORD记录
ord-c87ada3ed37b452fbec27d14d79e9694
来源数据集
uspto-grants-2013_09
专利号
US08530492B2

关联笔记

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